Novel heterocyclic compound and organic light emitting device comprising the same

ABSTRACT

Provided is a heterocyclic compound of Chemical Formula 1: 
     
       
         
         
             
             
         
       
         
         
           
             wherein:
           X 1  is O or S;   L 1  is a single bond or an unsubstituted phenylene;   L 2  is a single bond, or a substituted or unsubstituted: phenylene, naphthylene, or biphenylenyl;   Y 1  to Y 3  are each independently N or CR 3 , where at least one is N;   Ar 1a  and Ar 1b  are each independently a substituted or unsubstituted: C 6-60  aryl or C 1-60  heteroaryl containing  1  to  3  heteroatoms selected from N, O and S;   
         
             R 1  and R 2  are each independently hydrogen, deuterium, cyano, or a substituted or unsubstituted C 1-10  alkyl; 
             each R 3  is independently hydrogen, deuterium, halogen, cyano, nitro, amino, or a substituted or unsubstituted: C 1-60  alkyl, C 1-60  haloalkyl, C 1-60  alkoxy, a C 1-60  haloalkoxy, C 3-60  cycloalkyl, C 2-60  alkenyl, C 6-60  aryl, C 6-60  aryloxy, or a C 1-60  heteroaryl containing at least one heteroatom selected from N, O and S; 
             and an organic light emitting device comprising the same.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation of co-pending U.S. patent applicationSer. No. 15/771,066, which is the U.S. National Stage Application ofInternational Application No. PCT/KR2017/006274, filed Jun. 15, 2017,which claims the benefit of Korean Patent Application No.10-2016-0092202 filed on Jul. 20, 2016, and Korean Patent ApplicationNo. 10-2017-0075029 filed on Jun. 14, 2017, the disclosures of each ofwhich are incorporated herein by reference in their entirety for allpurposes as if fully set forth below.

TECHNICAL FIELD

The present invention relates to a novel heterocyclic compound and anorganic light emitting device comprising the same.

BACKGROUND

In general, an organic light emitting phenomenon refers to a phenomenonwhere electric energy is converted into light energy by using an organicmaterial. The organic light emitting device using the organic lightemitting phenomenon has characteristics such as a wide viewing angle, anexcellent contrast, a fast response time, excellent luminance, drivingvoltage and response speed, and thus many studies have proceeded.

The organic light emitting device generally has a structure whichcomprises an anode, a cathode, and an organic material layer interposedbetween the anode and the cathode. The organic material layer frequentlyhave a multilayered structure that comprises different materials inorder to enhance efficiency and stability of the organic light emittingdevice, and for example, the organic material layer may be formed of ahole injection layer, a hole transport layer, a light emitting layer, anelectron transport layer, an electron injection layer and the like. Inthe structure of the organic light emitting device, if a voltage isapplied between two electrodes, the holes are injected from an anodeinto the organic material layer and the electrons are injected from thecathode to the organic material layer, and when the injected holes andthe electrons meet each other, an exciton is formed, and light isemitted when the exciton falls to a ground state again.

There is a continuing demand for developing a new material for organicmaterials used in such organic light emitting devices.

PRIOR ART LITERATURE Patent Literature

(Patent Literature 1) Korean Patent Laid-open Publication No.10-2000-0051826

BRIEF DESCRIPTION Technical Problem

It is one object of the present invention to provide a novelheterocyclic compound and an organic light emitting device comprisingthe same.

Technical Solution

The present invention provides a compound represented by the followingChemical Formula 1:

In Chemical Formula 1,

X₁ is O or S,

L₁ and L₂ are each independently a single bond; a substituted orunsubstituted C₆₋₆₀ arylene; or a substituted or unsubstituted C₁₋₆₀heteroarylene containing one or more heteroatoms selected from the groupconsisting of O, N, Si and S,

Y₁ to Y₃ are each independently N or CR₃, provided that at least one ofY₁ to Y₃ is N,

Ar_(1a) and Ar_(1b) are each independently a substituted orunsubstituted C₆₋₆₀ aryl; or a substituted or unsubstituted C₁₋₆₀heteroaryl containing 1 to 3 heteroatoms selected from the groupconsisting of N, O and S,

Ar₂ is a substituted or unsubstituted C₆₋₆₀ aryl,

R₁ to R₃ are each independently hydrogen; deuterium; halogen; cyano;nitro; amino; a substituted or unsubstituted C₁₋₆₀ alkyl; a substitutedor unsubstituted C₁₋₆₀ haloalkyl; a substituted or unsubstituted C₁₋₆₀alkoxy; a substituted or unsubstituted C₁₋₆₀ haloalkoxy; a substitutedor unsubstituted C₃₋₆₀ cycloalkyl; a substituted or unsubstituted C₂₋₆₀alkenyl; a substituted or unsubstituted C₆₋₆₀ aryl; a substituted orunsubstituted CF-so aryloxy; or a substituted or unsubstituted C₁₋₆₀heteroaryl containing at least one heteroatom selected from the groupconsisting of N, O and S, and

n₁ and n₂ are each independently an integer of 0 to 3.

In addition, the present invention provides an organic light emittingdevice comprising a first electrode; a second electrode provided to facethe first electrode; and one or more organic material layers providedbetween the first electrode and the second electrode, wherein one ormore of the organic layers comprises a compound represented by ChemicalFormula 1.

Advantageous Effects

The compound represented by Chemical Formula 1 can be used as a materialof an organic material layer of an organic light emitting device and canexhibit improved efficiency, a low driving voltage and/or improvedlifetime characteristics of the organic light emitting device. Inparticular, the compound represented by Chemical Formula 1 can be usedas a host material of the light emitting layer.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 shows an example of an organic light emitting device comprising asubstrate 1, an anode 2, a light emitting layer 3, and a cathode 4.

FIG. 2 shows an example of an organic light emitting element comprisinga substrate 1, an anode 2, a hole injection layer 5, a hole transportlayer 6, a light emitting layer 7, an electron transport layer 8 and acathode 4.

DETAILED DESCRIPTION

Hereinafter, the present invention will be described in more detail tohelp understanding of the present invention.

In the present specification,

means a bond connected to another substituent group, and a single bondmeans when a separate atom does not exist in a portion denoted by L₁ andL₂.

As used herein, the term “substituted or unsubstituted” means thatsubstitution is performed by one or more substituent groups selectedfrom the group consisting of deuterium; a halogen group; a cyano group;a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; anester group; an imide group; an amino group; a phosphine oxide group; analkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxygroup; an alkylsulfoxy group; an arylsulfoxy group; a silyl group; aboron group; an alkyl group; a cycloalkyl group; an alkenyl group; anaryl group; an aralkyl groups; an aralkenyl group; an alkylaryl group;an alkylamine group; an aralkylamine group; a heteroarylamine group; anarylamine group; an arylphosphine group; or heteroaryl containing atleast one of N, O, and S atoms, or there is no substituent group, orsubstitution is performed by a substituent group where two or moresubstituent groups of the exemplified substituent groups are connectedor there is no substituent group. For example, the term “substituentgroup where two or more substituent groups are connected” may be abiphenyl group. That is, the biphenyl group may be an aryl group, or maybe interpreted as a substituent group where two phenyl groups areconnected.

In the present specification, the number of carbon atoms in a carbonylgroup is not particularly limited, but is preferably 1 to 40 carbonatoms. Specifically, the carbonyl group may be compounds having thefollowing structures, but is not limited thereto:

In the present specification, oxygen of an ester group may besubstituted by a straight-chain, branched-chain, or cyclic alkyl grouphaving 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbonatoms. Specifically, the ester group may be compounds having thefollowing structures, but is not limited thereto:

In the present specification, the number of carbon atoms in an imidegroup is not particularly limited but is preferably 1 to 25.Specifically, the imide group may be compounds having the followingstructures, but is not limited thereto:

In the present specification, the silyl group specifically includes atrimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilylgroup, a vinyldimethylsilyl group, a propyldimethylsilyl group, atriphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, andthe like, but is not limited thereto.

In the present specification, the boron group specifically includes atrimethylboron group, a triethylboron group, a t-butyldimethylborongroup, a triphenylboron group, a phenylboron group, and the like, but isnot limited thereto.

In the present specification, examples of a halogen group includefluorine, chlorine, bromine, or iodine.

In the present specification, an alkyl group may be a straight chain ora branched chain, and the number of carbon atoms thereof is notparticularly limited but is preferably 1 to 40. According to oneembodiment, the alkyl group has 1 to 20 carbon atoms. According toanother embodiment, the alkyl group has 1 to 10 carbon atoms. Accordingto still another embodiment, the alkyl group has 1 to 6 carbon atoms.Specific examples of the alkyl group include methyl, ethyl, propyl,n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl,1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl,tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl,4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl,1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl,tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl,2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl,2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are notlimited thereto.

In the present specification, the alkenyl group may be a straight chainor a branched chain, and the number of carbon atoms thereof is notparticularly limited but is preferably 2 to 40. According to oneembodiment, the alkenyl group has 2 to 20 carbon atoms. According toanother embodiment, the alkenyl group has 2 to 10 carbon atoms.According to still another embodiment, the alkenyl group has 2 to 6carbon atoms. Specific examples thereof include vinyl, 1-propenyl,isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl,3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl,1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl,2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl,a stilbenyl group, a styrenyl group, and the like, but are not limitedthereto.

In the present specification, a cycloalkyl group is not particularlylimited, but the number of carbon atoms thereof is preferably 3 to 60.According to one embodiment, the cycloalkyl group has 3 to 30 carbonatoms. According to another embodiment, the cycloalkyl group has 3 to 20carbon atoms. According to another embodiment, the cycloalkyl group has3 to 6 carbon atoms. Specific examples thereof include cyclopropyl,cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl,cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl,2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl,4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but arenot limited thereto.

In the present specification, the aryl group is not particularlylimited, but preferably has 6 to 60 carbon atoms, and may be amonocyclic aryl group or a polycyclic aryl group. According to oneembodiment, the aryl group has 6 to 30 carbon atoms. According to oneembodiment, the aryl group has 6 to 20 carbon atoms. The aryl group maybe a phenyl group, a biphenyl group, a terphenyl group or the like asthe monocyclic aryl group, but is not limited thereto. Examples of thepolycyclic aryl group include a naphthyl group, an anthracenyl group, aphenanthryl group, a pyrenyl group, a perylenyl group, a chrysenylgroup, a fluorenyl group or the like, but is not limited thereto.

In the present specification, a fluorenyl group may be substituted, andtwo substituent groups may be bonded to each other to form a spirostructure. In the case where the fluorenyl group is substituted,

and the like can be formed. However, the structure is not limitedthereto.

In the present specification, the heterocyclic group is a heterocyclicgroup containing one or more of O, N, Si and S as a heteroatom, and thenumber of carbon atoms thereof is not particularly limited, but ispreferably 2 to 60. Examples of the heterocyclic group include athiophene group, a furan group, a pyrrole group, an imidazole group, atriazole group, an oxazole group, an oxadiazole group, a triazole group,a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group,a triazole group, an acridyl group, a pyridazine group, a pyrazinylgroup, a quinolinyl group, a quinazoline group, a quinoxalinyl group, aphthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group,a pyrazinopyrazinyl group, an isoquinoline group, an indole group, acarbazole group, a benzoxazole group, a benzimidazole group, abenzothiazole group, a benzocarbazole group, a benzothiophene group, adibenzothiophene group, a benzofuranyl group, a phenanthroline group, athiazolyl group, an isoxazolyl group, an oxadiazolyl group, athiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, adibenzofuranyl group, and the like, but are not limited thereto.

In the present specification, the aryl group in the aralkyl group, thearalkenyl group, the alkylaryl group, and the arylamine group is thesame as the aforementioned examples of the aryl group. In the presentspecification, the alkyl group in the aralkyl group, the alkylaryl groupand the alkylamine group is the same as the aforementioned examples ofthe alkyl group. In the present specification, the heteroaryl in theheteroarylamines can be applied to the aforementioned description of theheterocyclic group. In the present specification, the alkenyl group inthe aralkenyl group is the same as the aforementioned examples of thealkenyl group. In the present specification, the aforementioneddescription of the aryl group may be applied except that the arylene isa divalent group. In the present specification, the aforementioneddescription of the heterocyclic group can be applied except that theheteroarylene is a divalent group. In the present specification, theaforementioned description of the aryl group or cycloalkyl group can beapplied except that the hydrocarbon ring is not a monovalent group butformed by combining two substituent groups. In the presentspecification, the aforementioned description of the heterocyclic groupcan be applied, except that the heterocycle is not a monovalent groupbut formed by combining two substituent groups.

Meanwhile, the present invention also provides a compound represented byChemical Formula 1.

Specifically, the compound represented by Chemical Formula 1 can berepresented by the following Chemical Formulas 1-1 to 1-4:

In the above chemical formulas 1-1 to 1-4, L₁, L₂, Y₁ to Y₃, Ar_(1a),Ar_(1b), Ar₂, R₁, R₂, n1 and n2 are as defined in Chemical Formula 1.

Preferably, in Chemical Formula 1, L₁ and L₂ are each independently asingle bond; or a substituted or unsubstituted C₆₋₂₀ arylenyl.

For example, L₁ and L₂ are each independently a single bond; asubstituted or unsubstituted phenylene; a substituted or unsubstitutednaphthylene; or a substituted or unsubstituted biphenylenyl.

Specifically, for example, L₁ and L₂ may each independently be a singlebond, or any one selected from the group consisting of:

Preferably, in Chemical Formula 1,

Y₁ is N, Y₂ is N, and Y₃ is N; or

Y₁ is N, Y₂ is N, and Y₃ is CR₃; or

Y₁ is N, Y₂ is CR₃, and Y₃ is N; or

Y₁ is N, Y₂ is CR₃, and Y₃ or CR₃; or

Y₁ is CR₃, Y₂ is CR₃, and Y₃ is N.

Preferably, in Chemical Formula 1,

Y₁ is N, Y₂ is N, and Y₃ is N; or

Y₁ is N, Y₂ is N, and Y₃ is CH; or

Y₁ is N, Y₂ is CH, and Y₃ is N; or

Y₁ is N, Y₂ is CH, and Y₃ is CH; or

Y₁ is CH, Y₂ is CH, and Y₃ is N.

Preferably, in Chemical Formula 1, Ar_(1a) and Ar_(1b) are eachindependently a substituted or unsubstituted C₆₋₂₀ aryl; or asubstituted or unsubstituted C₁₋₂₀ heteroaryl containing one heteroatomselected from the group consisting of N, O, and S.

For example, Ar₁₁ and Ar_(1b) may be each independently any one selectedfrom the group consisting of:

wherein,

X₂ is O, S, NZ₄, or CZ₅Z₆,

Z₁ to Z₆ are each independently hydrogen; deuterium; halogen; cyano;nitro; amino; a substituted or unsubstituted C₁₋₂₀ alkyl, a substitutedor unsubstituted C₁₋₂₀ haloalkyl, a substituted or unsubstituted C₁₋₂₀aryl, or a substituted or unsubstituted C₁₋₂₀ heteroaryl containing oneor more heteroatoms selected from the group consisting of N, O and S,

c1 is an integer of 0 to 5,

c2 is an integer of 0 to 4, and

c3 is an integer of 0 to 3.

In this case, c1 represents the number of Z₁, and when c1 is 2 or more,two or more Z₁ may be the same as or different from each other. Thedescription of c2 and c3 can be understood with reference to thedescription of c1 and the structure of the above chemical formula.

Specifically, for example, Ar_(1a) and Ar_(1b) may be each independentlyany one selected from the group consisting of:

Further, in Chemical Formula 1, Ar₂ is substituted or unsubstitutedC₆₋₆₀ aryl. Here, aryl does not include non-aromatic condensed rings.Specifically, a substituted or unsubstituted fluorenyl group is excludedfrom Ar₂ of the present invention.

Preferably, Ar₂ is a C₆₋₆₀ aryl which unsubstituted or substituted by asubstituent independently selected from the group consisting of:deuterium; halogen; cyano; nitro; amino; a substituted or unsubstitutedC₁₋₆₀ alkyl; a substituted or unsubstituted C₁₋₆₀ haloalkyl;Si(Q₁)(Q₂)(Q₃); C(Q₄)(Q₅)(Q₆) and C₆₋₆₀ aryl, wherein Q₁ to Q₆ are eachindependently hydrogen; deuterium; halogen;

cyano; nitro; amino; a substituted or unsubstituted C₁₋₂₀ alkyl; or asubstituted or unsubstituted C₆₋₂₀ aryl.

For example, Ar₂ may be any one selected from the group consisting of:

wherein

Z₁₁ to Z₁₄ are each independently hydrogen; deuterium; halogen; cyano;nitro; amino; a substituted or unsubstituted C₁₋₆₀ alkyl; a substitutedor unsubstituted C₁₋₆₀ haloalkyl; Si(Q₁)(Q₂)(Q₃); C(Q₄)(Q)(Q₆) and C₆₋₆₀aryl,

-   -   wherein Q₁ to Q₆ are each independently hydrogen: deuterium;        halogen; cyano: nitro; amino; a substituted or unsubstituted        C₁₋₂₀ alkyl; or a substituted or unsubstituted C₆₋₂₀ aryl,

c11 is an integer of 0 to 5,

c12 is an integer of 0 to 7,

c13 is an integer of 0 to 9,

c14 is an integer of 0 to 4,

c15 is an integer of 0 to 3,

c16 is an integer of 0 to 11,

c17 is an integer of 0 to 9,

c18 is an integer of 0 to 6, and

c19 is an integer of 0 to 12.

Here, c11 represents the number of Z₁₁, and when c11 is 2 or more, twoor more Z₁₁ may be the same as or different from each other. Thedescription of c12 to c19 can be understood with reference to thedescription of c11 and the structure of the above chemical formula.

Preferably, Q₁ to Q₆ are hydrogen; deuterium; halogen; cyano; nitro;amino; methyl; or phenyl.

Specifically, for example, Ar₂ may be any one selected from the groupconsisting of:

Further, in Chemical Formula 1, R₁ to R₃ are each independentlyhydrogen; deuterium; cyano; or a substituted or unsubstituted C₁₋₁₀alkyl.

For example, R₁ and R₂ may be each independently hydrogen, deuterium,cyano, methyl, or deuterium-substituted methyl, and R₃ may be hydrogen.

In Chemical Formula 1, n1 represents the number of R₁, and when n1 is 2or more, two or more R₁ may be the same as or different from each other.The description of n2 can be understood with reference to thedescription of n1 and the structure of Chemical Formula 1.

For example, the compound may be selected from the group consisting ofthe following compounds:

The compound represented by Chemical Formula 1 has a structure in whichan N-atom-containing heteroaryl substituent group such as a pyridinylgroup, a pyrimidinyl group, or a triazinyl group is connected to aspecific position of dibenzofuran or dibenzothiophene core, and an arylsubstituent group which is an aromatic group is connected to a specificposition of the dibenzofuran or dibenzothiophene core, and thereby anorganic light emitting device using the same has a higher efficiency, alower driving voltage and a longer life time than an organic lightemitting device using a compound in which a non-aromatic condensed ringgroup such as a fluorenyl group is connected.

Meanwhile, the compound represented by Chemical Formula 1 can beprepared in the same manner as shown in the following Reaction Scheme 1:

In Reaction Scheme 1, L₁, L₂, Y₁ to Y₃, Ar_(1a), Ar_(1b) and Ar₂ are asdefined in Chemical Formula 1.

The compound represented by Chemical Formula 1 can be prepared byappropriately substituting the starting material in accordance with thestructure of the compound to be prepared with reference to ReactionScheme 1.

In addition, the present invention provides an organic light emittingdevice comprising the compound represented by Chemical Formula 1. In oneexample, the present invention provides an organic light emitting devicecomprising: a first electrode; a second electrode provided to face thefirst electrode; and one or more organic material layers providedbetween the first electrode and the second electrode, wherein one ormore of the organic material layers comprise the compound of ChemicalFormula 1.

The organic material layer of the organic light emitting device of thepresent invention may have a single layer structure, or a multilayeredstructure in which two or more organic material layers are laminated.For example, the organic light emitting device of the present inventionmay have a structure including a hole injection layer, a hole transportlayer, a light emitting layer, an electron transport layer, an electroninjection layer, and the like as the organic material layer. However,the structure of the organic light emitting device is not limitedthereto, but may include a smaller number of organic layers.

Specifically, the organic material layer may include a light emittinglayer, and the light emitting layer includes the compound represented byChemical Formula 1.

In this case, the compound represented by Chemical Formula 1 can be usedas a host material in the light emitting layer.

Further, the organic light emitting device according to the presentinvention may be an organic light emitting device having a structure(normal type) where an anode, one or more organic material layers, and acathode are sequentially laminated on a substrate. Further, the organiclight emitting device according to the present invention may be anorganic light emitting device having an inverted direction structure(inverted type) where the cathode, one or more organic material layers,and the anode are sequentially laminated on the substrate. For example,the structure of the organic light emitting device according to oneembodiment of the present invention is illustrated in FIGS. 1 and 2.

FIG. 1 illustrates an example of an organic light emitting deviceincluding a substrate 1, an anode 2, a light emitting layer 3, and acathode 4. In such a structure, the compound represented by ChemicalFormula 1 may be included in the light emitting layer.

FIG. 2 illustrates an example of an organic light emitting deviceincluding a substrate 1, an anode 2, a hole injection layer 5, a holetransport layer 6, a light emitting layer 7, an electron transport layer8, and a cathode 4. In such a structure, the compound represented byChemical Formula 1 may be included in one or more layers of the holeinjection layer, the hole transport layer, the light emitting layer, andthe electron transport layer.

The organic light emitting device according to the present invention maybe manufactured by using materials and methods known in the art, exceptthat one or more of organic material layers include the compoundrepresented by Chemical Formula 1. Further, in the case where theorganic light emitting device includes a plurality of organic materiallayers, the organic material layers may be formed of the same materialsor different materials.

For example, the organic light emitting device according to the presentinvention may be manufactured by sequentially laminating the firstelectrode, the organic material layer, and the second electrode on thesubstrate. In this case, the organic light emitting device may bemanufactured by depositing a metal, metal oxides having conductivity, oran alloy thereof on the substrate by using a PVD (physical vapordeposition) method such as a sputtering method or an e-beam evaporationmethod to form the anode, forming the organic material layer includingthe hole injection layer, the hole transport layer, the light emittinglayer, and the electron transport layer thereon, and then depositing amaterial that can be used as the cathode thereon. In addition to such amethod, the organic light emitting device may be manufactured bysequentially depositing a cathode material, the organic material layer,and an anode material on the substrate.

Further, the compound represented by Chemical Formula 1 may be formed asthe organic material layer by a vacuum deposition method as well as asolution coating method during the production of the organic lightemitting device. Herein, the solution coating method means spin coating,dip coating, doctor blading, inkjet printing, screen printing, a spraymethod, roll coating, or the like, but is not limited thereto.

In addition to such a method, the organic light emitting device may bemanufactured by sequentially depositing a cathode material, an organicmaterial layer, and an anode material on a substrate (InternationalPublication WO 2003/012890). However, the manufacturing method is notlimited thereto.

In one example, the first electrode is the anode, and the secondelectrode is the cathode, and alternatively, the first electrode is thecathode, and the second electrode is the anode.

As the anode material, generally, a material having a large workfunction is preferably used so that holes can be smoothly injected intothe organic material layer. Specific examples of the anode materialinclude metals such as vanadium, chrome, copper, zinc, and gold, or analloy thereof; metal oxides such as zinc oxides, indium oxides, indiumtin oxides (ITO), and indium zinc oxides (IZO); a combination of metalsand oxides, such as ZnO:Al or SNO₂:Sb; conductive polymers such aspoly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT),polypyrrole, and polyaniline, and the like, but are not limited thereto.

As the cathode material, generally, a material having a small workfunction is preferably used so that electrons can be easily injectedinto the organic material layer. Specific examples of the cathodematerial include metals such as magnesium, calcium, sodium, potassium,titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin,and lead, or an alloy thereof; a multilayered structure material such asLiF/Al or LiO₂/Al, and the like, but are not limited thereto.

The hole injection material layer is a layer injecting the holes fromthe electrode, and the hole injection material is preferably a compoundwhich has an ability of transporting the holes, a hole injection effectin the anode and an excellent hole injection effect to the lightemitting layer or the light emitting material, prevents movement of anexciton generated in the light emitting layer to the electron injectionlayer or the electron injection material, and has an excellent thin filmforming ability. It is preferable that a HOMO (highest occupiedmolecular orbital) of the hole injection material is between the workfunction of the anode material and a HOMO of a peripheral organicmaterial layer. Specific examples of the hole injection material includemetal porphyrine, oligothiophene, an arylamine-based organic material, ahexanitrilehexaazatriphenylene-based organic material, aquinacridone-based organic material, a perylene-based organic material,anthraquinone, polyaniline and polythiophene-based conductive polymer,and the like, but are not limited thereto.

The hole transport layer is a layer receiving the holes from the holeinjection layer and transporting the holes to the light emitting layer,and the hole transport material is a material that can receive the holesfrom the anode or the hole injection layer and transport the holes tothe light emitting layer, and a material having large mobility to theholes is suitable. Specific examples thereof include an arylamine-basedorganic material, a conductive polymer, a block copolymer in which aconjugate portion and a non-conjugate portion are present together, andthe like, but are not limited thereto.

The light emitting material layer is a material that can receive theholes and the electrons from the hole transport layer and the electrontransport layer, respectively, and bond the holes and the electrons toemit light in a visible ray region, and is preferably a material havinggood quantum efficiency to fluorescence or phosphorescence. Specificexamples thereof include a 8-hydroxy-quinoline aluminum complex (Alq₃);a carbazole-based compound; a dimerized styryl compound; BAlq; a10-hydroxybenzoquinoline-metal compound; benzoxazole, benzothiazole, andbenzimidazole-based compounds; a poly(p-phenylenevinylene) (PPV)-basedpolymer; a spiro compound; polyfluorene, rubrene, and the like, but arenot limited thereto.

The light emitting layer may include a host material and a dopantmaterial. Examples of the host material include a condensation aromaticcycle derivative, a heterocycle-containing compound, or the like.Specific examples of the condensation aromatic cycle derivative includean anthracene derivative, a pyrene derivative, a naphthalene derivative,a pentacene derivative, a phenanthrene compound, a fluoranthenecompound, and the like, and specific examples of theheterocycle-containing compound include a carbazole derivative, adibenzofuran derivative, a ladder-type furan compound, a pyrimidinederivative, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, astyrylamine compound, a boron complex, a fluoranthene compound, a metalcomplex, and the like. Specifically, the aromatic amine derivative is acondensation aromatic cycle derivative having a substituted orunsubstituted arylamino group, examples thereof include pyrene,anthracene, chrysene, and periflanthene having the arylamino group, andthe like, the styrylamine compound is a compound where at least onearylvinyl group is substituted in substituted or unsubstitutedarylamine, in which one or two or more substituent groups selected fromthe group consisting of an aryl group, a silyl group, an alkyl group, acycloalkyl group, and an arylamino group are substituted orunsubstituted. Specific examples thereof include styrylamine,styryldiamine, styryltriamine, styryltetramine, and the like, but arenot limited thereto. Further, examples of the metal complex include aniridium complex, a platinum complex, and the like, but are not limitedthereto.

The electron transport material is a layer receiving the electrons fromthe electron injection layer and transporting the electrons to the lightemitting layer, the electron transport material is a material that canreceive the electrons well from the cathode and transport the electronsto the light emitting layer, and a material having large mobility to theelectrons is suitable. Specific examples thereof include an8-hydroxyquinoline Al complex; a complex including Alq₃; an organicradical compound; a hydroxyflavone-metal complex, and the like, but arenot limited thereto. Particularly, it is preferable to use the compoundrepresented by the above-mentioned chemical formula 1 as an electrontransport material. The electron transport layer may be used togetherwith a predetermined desired cathode material as used according to theprior art. Particularly, an example of an appropriate cathode materialis a general material having the low work function and followed by analuminum layer or a silver layer. Specific examples thereof includecesium, barium, calcium, ytterbium, and samarium, and each case isfollowed by the aluminum layer or the silver layer.

The electron injection layer is a layer injecting the electrons from theelectrode, and a compound which has an ability of transporting theelectrons, an electron injection effect from the cathode, and anexcellent electron injection effect to the light emitting layer or thelight emitting material, prevents movement of an exciton generated inthe light emitting layer to the hole injection layer, and has anexcellent thin film forming ability is preferable. Specific examplesthereof include fluorenone, anthraquinodimethane, diphenoquinone,thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and the like,and derivatives thereof, a metal complex compound, a nitrogen-containing5-membered cycle derivative, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinatolithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper,bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum,tris(2-methyl-8-hydroxyquinolinato)aluminum,tris(8-hydroxyquinolinato)gallium,bis(10-hydroxybenzo[h]quinolinato)beryllium,bis(10-hydroxybenzo[h]quinolinato)zinc,bis(2-methyl-8-quinolinato)chlorogallium,bis(2-methyl-8-quinolinato)(o-cresolato)-gallium,bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum,bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, and the like, but arenot limited thereto.

The organic light emitting device according to the present invention maybe a front side emission type, a back side emission type, or a doubleside emission type according to the used material.

Further, the compound represented by Chemical Formula 1 may be includedin an organic solar cell or an organic transistor in addition to theorganic light emitting device.

The preparation of the compound represented by Chemical Formula 1 andthe organic light emitting device including the same will be describedin detail in the following examples. However, these examples arepresented for illustrative purposes only, and the scope of the presentinvention is not limited thereto.

Synthesis Example 1: Preparation of Intermediate Compound P-6

1-Bromo-3-fluoro-2-iodobenzene (100 g, 333.5 mmol) and(5-chloro-2-methoxyphenyl)boronic acid (62.2 g, 333.5 mmol) weredissolved in 800 ml of tetrahydrofuran (THF). Then, 2M sodium carbonate(Na₂CO₃) solution (500 mL) and tetrakis(triphenylphosphine)palladium(0)[Pd(PPh₃)₄] (7.7 g, 6.7 mmol) were added thereto, and the mixture wasrefluxed for 12 hours. After completion of the reaction, the mixture wascooled to room temperature, and then was extracted three times withwater and toluene. The toluene layer was separated and dried withmagnesium sulfate, and the filtrate was distilled under reducedpressure. The resulting mixture was recrystallized three times usingchloroform and ethanol to obtain Compound P-1 (53.7 g, yield 51%; MS:[M+H]⁺=314),

Compound P-1 (50.0 g, 158.5 mmol) was dissolved in dichloromethane (600ml) and then cooled to 0° C. Boron tribromide (15.8 ml, 166.4 mmol) wasslowly added dropwise thereto and then stirred for 12 hours. Aftercompletion of the reaction, the mixture was washed three times withwater, dried with magnesium sulfate, and filtered. The filtrate wasdistilled under reduced pressure and purified by column chromatographyto obtain Compound P-2 (47.4 g, yield 99%; MS:[M+H]⁺=300).

Compound P-2 (40.0 g, 132.7 mmol) was dissolved in distilleddimethylformamide (DMF) (400 ml). This solution was cooled to 0° C. andsodium hydride (3.5 g, 145.9 mmol) was slowly added dropwise thereto.After stirring for 20 minutes, the mixture was stirred at 100° C. for 1hour. After completion of the reaction, the reaction mixture was cooledto room temperature and 100 ml of ethanol was slowly added. The mixturewas distilled under reduced pressure, and the resulting mixture wasrecrystallized from chloroform and ethyl acetate to obtain Compound P-3(30.3 g, yield 81%: MS: [M+H]⁺=280).

After Compound P-3 (30.0 g, 106.6 mmol) was dissolved in tetrahydrofuran(300 ml), the temperature was lowered to −78° C. and 1.7Mtert-butyllithium (t-BuLi) (62.7 ml, 106.6 mmol) was slowly added. Afterstirring at the same temperature for one hour, triisopropyl borate(B(OiPr)₃) (28.3 ml, 213.1 mmol) was added and stirred for 3 hours whilegradually increasing the temperature to room temperature. To thereaction mixture was added 2N aqueous hydrochloric acid solution (200mil) and then stirred at room temperature for 1.5 hours. The resultingprecipitate was filtered, washed sequentially with water and ethylether, and dried under vacuum. After drying, the mixture was dispersedin ethyl ether, stirred for 2 hours, filtered and dried to obtainCompound P-4 (24.4 g, yield 93%; MS: [M+H]⁺=247).

After Compound P-4 (20.0 g, 81.2 mmol) and2-chloro-4,6-diphenyl-1,3,5-triazine (21.8 g, 81.2 mmol) were dispersedin tetrahydrofuran (250 ml), 2M aqueous potassium carbonate solution(aq. K₂CO₃) (33.6 ml, 243.5 mmol) was added,tetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄] (1.9 g, 2 mol %) wasadded, and then the mixture was stirred and refluxed for 4 hours. Thetemperature was lowered to room temperature and the resulting solid wasfiltered. The filtrated solid was recrystallized from tetrahydrofuranand ethyl acetate, filtered and then dried to obtain Compound P-5 (32.4g, yield 92%; MS:[M+H]⁺=434).

Compound P-5 (30 g, 69.2 mmol), bis(pinacolato)diboron (19.3 g, 76.1mmol), potassium acetate (20.4 g, 207.5 mmol), and tetrakis(triphenylphosphine)palladium(0) [Pd(PPh₃)₄] (1.6 g, 2 mol %) was addedto tetrahydrofuran (300 ml) and refluxed for 12 hours. After completionof the reaction, the mixture was cooled to room temperature anddistilled under reduced pressure to remove the solvent. This wasdissolved in chloroform, washed three times with water, and then theorganic layer was separated, dried with magnesium sulfate and thendistilled under reduced pressure to obtain Compound P-6 (34.5 g, yield95%; MS: [M+H]⁺=526).

Synthesis Example 1-1: Preparation of Compound 1

After Compound P-6 (20.0 g, 38.1 mmol) and 2-bromophenanthrene (9.8 g,38.1 mmol) were dispersed in tetrahydrofuran (250 ml), 2M aqueouspotassium carbonate solution (aq. K₂CO₃) (57.2 ml, 114.3 mmol) was addedand tetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄] (1.4 g, 2 mol %)was added, and then the mixture was stirred and refluxed for 5 hours.The temperature was lowered to room temperature and the resulting solidwas filtered. The filtered solid was recrystallized from chloroform andethyl acetate, filtered and then dried to obtain Compound 1 (17.8 g,yield 81%; MS: [M+H]⁺=576).

Synthesis Example 1-2: Preparation of Compound 2

Compound 2 (18.4 g, yield 84%; MS:[M+H]⁺=576) was prepared in the samemanner as in Synthesis Example 1-1, except that 9-bromophenanthrene (9.8g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-3: Preparation of Compound 3

Compound 3 (18.8 g, yield 82%; MS:[M+H]⁺=602) was prepared in the samemanner as in Synthesis Example 1-1, except that1-bromo-4-phenylnaphthalene (10.8 g, 38.1 mmol) was used instead of2-bromophenanithrene.

Synthesis Example 1-4: Preparation of Compound 4

Compound 4 (21.0 g, yield 88%; MS:[M+H]⁺=626) was prepared in the samemanner as in Synthesis Example 1-1, except that 2-bromotriphenylene(11.7 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-5: Preparation of Compound 11

Compound 11 (19.9 g, yield 80%; MS:[M+H]⁺=652) was prepared in the samemanner as in Synthesis Example 1-1, except that9-(4-bromophenyl)phenanthrene (12.7 g, 38.1 mmol) was used instead of2-bromophenanthrene.

Synthesis Example 1-6: Preparation of Compound 12

Compound 12 (22.5 g, yield 81%; MS:[M+H]⁺=728) was prepared in the samemanner as in Synthesis Example 1-1, except that9-(2′-bromo-[1,1′-biphenyl]-2-yl)phenanthrene (15.6 g, 38.1 mmol) wasused instead of 2-bromophenanthrene.

Synthesis Example 1-7: Preparation of Compound 13

Compound 13 (21.8 g, yield 76%; MS:[M+H]⁺=752) was prepared in the samemanner as in Synthesis Example 1-1, except that7-(4-bromophenyl)-10-phenylfluoranthene (16.5 g, 38.1 mmol) was usedinstead of 2-bromophenanthrene.

Synthesis Example 1-8: Preparation of Compound 25

Compound 25 (24.3 g, yield 89%; MS:[M+H]⁺=718) was prepared in the samemanner as in Synthesis Example 1-1, except that((4-bromophenyl)methanetriyl)tribenzene (15.2 g, 38.1 mmol) was usedinstead of 2-bromophenanthrene.

Synthesis Example 1-9: Preparation of Compound 26

Compound 26 (19.9 g, yield 83%; MS:[M+H]⁺=628) was prepared in the samemanner as in Synthesis Example 1-1, except that4-bromo-1,1′:3′,1″-terphenyl (11.8 g, 38.1 mmol) was used instead of2-bromophenanthrene.

Synthesis Example 1-10: Preparation of Compound 28

Compound 28 (21.7 g, yield 81%; MS:[M+H]⁺=704) was prepared in the samemanner as in Synthesis Example 1-1, except that4-bromo-5′-phenyl-1,1′:3′,1″-terphenyl (14.7 g, 38.1 mmol) was usedinstead of 2-bromophenanthrene.

Synthesis Example 1-11: Preparation of Compound 46

Compound 46 (22.3 g, yield 83%; MS:[M+H]⁺=704) was prepared in the samemanner as in Synthesis Example 1-1, except that 4′″-bromo-1,1:3′,1:4,1′″-quaterphenyl (14.7 g, 38.1 mmol) was used instead of2-bromophenanthrene.

Synthesis Example 1-12: Preparation of Compound 55

Compound 55 (20.6 g, yield 86%; MS:[M+H]⁺=628) was prepared in the samemanner as in Synthesis Example 1-1, except that3-bromo-1,1′:4′,1″-terphenyl (11.8 g, 38.1 mmol) was used instead of2-bromophenanthrene.

Synthesis Example 1-13: Preparation of Compound 57

Compound 57 (20.4 g, yield 82%; MS:[M+H]⁺=652) was prepared in the samemanner as in Synthesis Example 1-1, except that9-(3-bromophenyl)phenanthrene (12.7 g, 38.1 mmol) was used instead of2-bromophenanthrene.

Synthesis Example 1-14: Preparation of Compound 62

Compound 62 (22.3 g, yield 83%; MS:[M+H]⁺=704) was prepared in the samemanner as in Synthesis Example 1-1, except that3-bromo-5′-phenyl-1,1:3′,1″-terphenyl (14.7 g, 38.1 mmol) was usedinstead of 2-bromophenanthrene.

Synthesis Example 1-15: Preparation of Compound 65

Compound 65 (21.7 g, yield 81%; MS:[M+H]⁺=704) was prepared in the samemanner as in Synthesis Example 1-1, except that5′-bromo-1,1:3,1″:3″,1″-quaterphenyl (14.7 g, 38.1 mmol) was usedinstead of 2-bromophenanthrene.

Synthesis Example 1-16: Preparation of Compound 66

Compound 66 (20.6 g, yield 77%; MS:[M+H]⁺=704) was prepared in the samemanner as in Synthesis Example 1-1, except that 2-bromo-1,1′:3′,1“:3”,1′″quaterphenyl (14.7 g, 38.1 mmol) was used instead of2-bromophenanthrene.

Synthesis Example 1-17: Preparation of Compound 68

Compound 68 (22.9 g, yield 79%; MS:[M+H]⁺=760) was prepared in the samemanner as in Synthesis Example 1-1, except that4,4′,4″-((4-bromophenyl)methanetriyl)tris(methylbenzene) (16.9 g, 38.1mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-18: Preparation of Compound 72

Compound 72 (20.7 g, yield 76%; MS:[M+H]⁺=714) was prepared in the samemanner as in Synthesis Example 1-1, except that5′-(4-bromophenyl)-1,1′:3′,1″-terphenyl-2,2″,3,3″,4,4″,5,5″,6,6″-d10(15.1 g, 38.1 mmol) was used instead of 2-bromophenanthrene.

Synthesis Example 1-19: Preparation of Compound 81

Compound 81 (18.9 g, yield 76%; MS:[M+H]⁺=652) was prepared in the samemanner as in Synthesis Example 1-1, except that3-(3-bromophenyl)phenanthrene (12.7 g, 38.1 mmol) was used instead of2-bromophenanthrene.

Synthesis Example 1-20: Preparation of Compound 59

Compound 59 (19.5 g, yield 73%; MS:[M+H]⁺=702) was prepared in the samemanner as in Synthesis Example 1-1, except that2-(3-bromophenyl)triphenylene (14.6 g, 38.1 mmol) was used instead of2-bromophenanthrene.

Synthesis Example 1-21: Preparation of Compound 45

Compound 45 (19.4 g, yield 81%; MS:[M+H]⁺=628) was prepared in the samemanner as in Synthesis Example 1-1, except that5′-bromo-1,1′:3′,1″-terphenyl (11.8 g, 38.1 mmol) was used instead of2-bromophenanthrene.

Synthesis Example 1-22: Preparation of Compound 54

Compound 54 (21.2 g, yield 79%; MS:[M+H]⁺=704) was prepared in the samemanner as in Synthesis Example 1-1, except that5′-bromo-1,1:3,1″:4″,1″-quaterphenyl (14.7 g, 38.1 mmol) was usedinstead of 2-bromophenanthrene.

Synthesis Example 1-23: Preparation of Compound 29

Compound 29 (15.6 g, yield 74%; MS:[M+H]⁺=552) was prepared in the samemanner as in Synthesis Example 1-1, except that 2-bromo-1,1′-biphenyl(8.9 g, 38.1 mmol) Was used instead of 2-bromophenanthrene.

Synthesis Example 2: Preparation of Intermediate Compound P-8

After Compound P-4 (40.0 g, 162.3 mmol) and2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (55.8 g, 162.3mmol) were dispersed in tetrahydrofuran (500 ml), 2M potassium carbonateaqueous solution (aq. K₂CO₃) (67.2 ml, 486.9 mmol) was added and thentetrakis(triphenylphosphine) palladium [Pd(PPh₃)₄] (3.8 g, 2 mol %) wasadded, and the mixture was stirred and refluxed for 4 hours. Thetemperature was lowered to room temperature and the resulting solid wasfiltered. The filtered solid was recrystallized from tetrahydrofuran andethyl acetate, filtered and then dried to obtain Compound P-7 (73.7 g,yield 89%; MS: [M+H]⁺=510).

Compound P-7 (70.5 g, 138.3 mmol), bis(pinacolato)diboron (38.6 g,152.13 mmol), potassium acetate (40.7 g, 414.9 mmol), andtetrakis(triphenylphosphine)palladium(0) [Pd(PPha)₄] (3.2 g, 2 mol %)were added to tetrahydrofuran (600 ml) and refluxed for 12 hours. Aftercompletion of the reaction, the reaction mixture was cooled to roomtemperature and distilled under reduced pressure to remove the solvent.This was dissolved in chloroform and washed three times with water. Theorganic layer was separated, dried with magnesium sulfate, and thendistilled under reduced pressure to obtain Compound P-8 (75.7 g, yield91%; MS: [M+H]⁺=602).

Synthesis Example 2-1: Preparation of Compound 9

Compound 9 (19.9 g, yield 77%; MS:[M+H]⁺=678) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound P-8 (22.9g, 38.1 mmol) instead of Compound P-6, and 2-(3-bromophenyl)naphthalene(10.8 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 2-2: Preparation of Compound 27

Compound 27 (21.2 g, yield 79%; MS:[M+H]⁺=704) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound P-8 (22.9g, 38.1 mmol) instead of Compound P-6, and 4-bromo-1,1′:4′,1″-terphenyl(11.8 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 3: Preparation of Intermediate Compound P-10

After Compound P-4 (40.0 g, 162.3 mmol) and2-([1,1′-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (55.8 g, 162.3mmol) were dispersed in tetrahydrofuran (500 ml), 2M potassium carbonateaqueous solution (aq. K₂CO₃) (67.2 ml, 486.9 mmol) was added andtetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄](3.8 g, 2 mol %) wasadded, and then the mixture was stirred and refluxed for 4 hours. Thetemperature was lowered to room temperature and the resulting solid wasfiltered. The filtrated solid was recrystallized from tetrahydrofuranand ethyl acetate, filtered and then dried to obtain Compound P-9 (69.5g, yield 84%; MS: [M+H]⁺=510).

Compound P-9 (70.5 g, 138.3 mmol) bis(pinacolato)diboron (38.6 g, 152.13mmol), potassium acetate (40.7 g, 414.9 mmol) and tetrakis(triphenylphosphine)palladium(0) [Pd(PPh₃)₄](3.2 g, 2 mol %) were addedto tetrahydrofuran (600 ml) and refluxed for 12 hours. After completionof the reaction, the reaction mixture was cooled to room temperature anddistilled under reduced pressure to remove the solvent. This wasdissolved in chloroform and washed three times with water. The organiclayer was separated, dried with magnesium sulfate, and distilled underreduced pressure to obtain Compound P-10 (73.5 g, yield 88%/o; MS:[M+H]⁺=602).

Synthesis Example 3-1: Preparation of Compound 6

Compound 6 (20.3 g, yield 76%; MS:[M+H]⁺=702) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound P-10 (22.9g, 38.1 mmol) instead of Compound P-6, and 2-bromotriphenylene (11.7 g,38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 3-2: Preparation of Compound 36

Compound 36 (21.1 g, yield 78%; MS:[M+H]⁺=709) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound P-10 (22.9g, 38.1 mmol) instead of Compound P-6, and4-bromo-1,1′:4′,1″-terphenyl-2″,3″,4″,5″,6″-d5 (12.0 g, 38.1 mmol)instead of 2-bromophenanthrene.

Synthesis Example 3-3: Preparation of Compound 49

Compound 49 (20.4 g, yield 71%; MS:[M+H]⁺=754) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound P-10 (22.9g, 38.1 mmol) instead of Compound P-6, and1-([1,1′-biphenyl]-2-yl)-4-bromonaphthalene (13.7 g, 38.1 mmol) insteadof 2-bromophenanthrene.

Synthesis Example 3-4: Preparation of Compound 61

Compound 61 (19.8 g, yield 74%; MS:[M+H]⁺=704) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound P-10 (22.9g, 38.1 mmol) instead of Compound P-6, and 4-bromo-1,1′:4′,1″-terphenyl(11.8 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 3-5: Preparation of Compound 70

Compound 70 (20.2 g, yield 68%; MS:[M+H]⁺=780) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound P-10 (22.9g, 38.1 mmol) instead of Compound P-6, and6′-bromo-1,1′:3′,1″:4″,1′″-quaterphenyl (14.7 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 4: Preparation of Intermediate Compound Q-4

Compound Q-1 (81.6 g, yield 87%; MS:[M+H]⁺=280) was prepared in the samemanner as in Synthesis Example 1-1, except that (2-methoxyphenyl)boronicacid (50.7 g, 333.5 mmol) was used instead of(5-chloro-2-methoxyphenyl)boronic acid (62.2 g, 333.5 mmol).

Compound Q-2 (71.2 g, yield 99%; MS:[M+H]⁺=266) was prepared in the samemanner as in Synthesis Example 1-1, except that Compound Q-1 (75.7 g,269.4 mmol) was used instead of Compound P-1 (85.0 g, 269.4 mmol).

Compound Q-3 (62.3 g, yield 95%; MS:[M+H]⁺=246) was prepared in the samemanner as in Synthesis Example 1-1, except that Compound Q-2 (70.9 g,265.3 mmol) was used instead of Compound P-2 (80.0 g, 265.3 mmol).

Compound Q-3 (40 g, 161.9 mmol) was dissolved in 200 ml of acetic acid,to which iodine (4.16 g, 81.0 mmol), iodic acid (6.3 g, 36.0 mmol) andsulfuric acid (10 mi) were added and stirred at 65° C. for 3 hours.After completion of the reaction, the mixture was cooled to roomtemperature and water was added. The resulting solid was filtered,washed with water and then recrystallized from toluene and ethyl acetateto obtain Compound Q-4 (50.1 g, yield 83%; MS: [M+H]⁺=372).

Synthesis Example 4-1: Preparation of Intermediate Compound Q-5

Compound Q-4 (30 g, 80.4 mmol) and4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g,80.4 mmol) were dissolved in 300 ml of tetrahydrofuran (THF), to which2M sodium carbonate (Na₂CO₃) solution (120 mL) and tetrakis(triphenylphosphine)palladium(0) [Pd(PPh₃)₄](1.9 g, 2 mol %) andrefluxed for 6 hours. After completion of the reaction, the mixture wascooled to room temperature, and the resulting mixture was extractedthree times with water and toluene. The toluene layer was separated anddried over magnesium sulfate.

The filtrate was distilled under reduced pressure, and the obtainedmixture was recrystallized from chloroform and ethyl acetate to obtainCompound Q-5 (28.9 g, yield 76%; MS: [M+H]⁺=473).

Synthesis Example 4-2: Preparation of Intermediate Compound Q-6

Compound Q-5 (25 g, 52.8 mmol), bis(pinacolato)diboron (14.9 g, 58.1mmol), potassium acetate (15.5 g, 158.4 mmol) andtetrakis(triphenylphosphine) palladium(0) [Pd(PPh₃)₄] (1.2 g, 2 mol %)was added to tetrahydrofuran (300 ml) and refluxed for 12 hours. Aftercompletion of the reaction, the mixture was cooled to room temperatureand distilled under reduced pressure to remove the solvent. This wasdissolved in chloroform and washed three times with water. The organiclayer was separated, dried with magnesium sulfate, and then distilledunder reduced pressure to obtain Compound Q-6 (25.0 g, yield 91%; MS:[M+H]⁺=521).

Synthesis Example 4-3: Preparation of Compound 7

Compound 7 (19.0 g, yield 71%; MS:[M+H]⁺=702) was prepared in the samemanner as in Synthesis Example 1-1, except for using2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine(16.6 g, 38.1 mmol) instead of Compound P-6, and Compound Q-5 (18.0 g,38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 4-4: Preparation of Compound 8

Compound 8 (19.9 g, yield 73%; MS:[M+H]⁺=716) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-6 (19.8g, 38.1 mmol) instead of Compound P-6, and2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (13.6 g,38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 4-5: Preparation of Compound 19

Compound 19 (19.5 g, yield 70%; MS:[M+H]⁺=732) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-6 (19.8g, 38.1 mmol) instead of Compound P-6, and2-chloro-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine (14.2 g,38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 4-6: Preparation of Compound 48

Compound 48 (22.3 g, yield 74%; MS:[M+H]⁺=791) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-6 (19.8g, 38.1 mmol) instead of Compound P-6, and4-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9-phenyl-9H-carbazole (16.5 g,38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 4-7: Preparation of Compound 58

Compound 58 (18.7 g, yield 62%; MS:[M+H]⁺=792) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-6 (19.8g, 38.1 mmol) instead of Compound P-6, and2-(2-bromophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine(18.2 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 5-1: Preparation of Intermediate Compound Q-7

Compound Q-7 (20.0 g, yield 59%; MS:[M+H]⁺=423) was prepared in the samemanner as in Synthesis Example 4-1, except that4,4,5,5-tetramethyl-2-(phenanthren-2-yl)-1,3,2-dioxaborolane (24.5 g,80.4 mmol) was used instead of4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g,80.4 mmol).

Synthesis Example 5-2: Preparation of Intermediate Compound Q-8

Compound Q-8 (21.6 g, yield 87%; MS:[M+H]⁺=471) was prepared in the samemanner as in Synthesis Example 4-2, except that Compound Q-7 (22.4 g,52.8 mmol) was used instead of Compound Q-5 (25 g, 52.8 mmol).

Synthesis Example 5-3: Preparation of Compound 10

Compound 10 (18.4 g, yield 65%; MS:[M+H]⁺=742) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-8 (17.9g, 38.1 mmol) instead of Compound P-6, and2-(4-chlorophenyl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine(16.5 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 5-4: Preparation of Compound 15

Compound 15 (15.8 g, yield 54%; MS:[M+H]⁺=768) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-8 (17.9g, 38.1 mmol) instead of Compound P-6, and2-chloro-4-(4-(9,9-dimethyl-9H-fluoren-1-yl)phenyl)-6-phenyl-1,3,5-triazine(17.5 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 6-1: Preparation of Intermediate Compound Q-9

Compound Q-9 (20.8 g, yield 61%; MS:[M+H]⁺=423) was prepared in the samemanner as in Synthesis Example 4-1, except that4,4,5,5-tetramethyl-2-(phenanthren-9-yl)-1,3,2-dioxaborolane (24.5 g,80.4 mmol) was used instead of4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g,80.4 mmol).

Synthesis Example 6-2: Preparation of Intermediate Compound Q-10

Compound Q-10 (21.1 g, yield 85%; MS:[M+H]⁺=471) was prepared in thesame manner as in Synthesis Example 4-2, except that Compound Q-7 (22.4g, 52.8 mmol) was used instead of Compound Q-5 (25 g, 52.8 mmol)

Synthesis Example 6-3: Preparation of Compound 50

Compound 50 (14.4 g, yield 51%; MS:[M+H]⁺=742) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-8 (17.9g, 38.1 mmol) instead of Compound P-6, and2-(3-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine(16.6 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 7-1: Preparation of Intermediate Compound Q-11

Compound Q-11 (23.6 g, yield 62%; MS:[M+H]⁺=473) was prepared in thesame manner as in Synthesis Example 4-1, except that2-(chrysen-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (28.4 g, 80.4mmol) was used instead of4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g,80.4 mmol).

Synthesis Example 7-2: Preparation of Intermediate Compound Q-12

Compound Q-12 (22.5 g, yield 82%; MS:[M+H]⁺=521) was prepared in thesame manner as in Synthesis Example 4-2, except that Compound Q-11 (25.0g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 7-3: Preparation of Compound 14

Compound 14 (14.5 g, yield 48%; MS:[M+H]⁺=792) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-12 (17.9g, 38.1 mmol) instead of Compound P-6, and2-(2-chlorophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine(16.5 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 8-1: Preparation of Intermediate Compound Q-13

Compound Q-13 (29.3 g, yield 73%; MS:[M+H]⁺=499) was prepared in thesame manner as in Synthesis Example 4-1, except that4,4,5,5-tetramethyl-2-(4-(phenanthren-9-yl)phenyl)-1,3,2-dioxaborolane(30.6 g, 80.4 mmol) was used instead of4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g,80.4 mmol).

Synthesis Example 8-2: Preparation of Intermediate Compound Q-14

Compound Q-14 (24.5 g, yield 85%; MS:[M+H]⁺=547) was prepared in thesame manner as in Synthesis Example 4-2, except that Compound Q-13 (26.4g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 8-3: Preparation of Compound 17

Compound 17 (18.9 g, yield 68%; MS:[M+H]⁺=728) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-14 (20.8g, 38.1 mmol) instead of Compound P-6, and2-([1,1′-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (13.1 g, 38.1mmol) instead of 2-bromophenanthrene.

Synthesis Example 9-1: Preparation of Intermediate Compound Q-15

Compound Q-15 (25.7 g, yield 80%; MS:[M+H]⁺=399) was prepared in thesame manner as in Synthesis Example 4-1, except that2-([1,1′-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (22.5g, 80.4 mmol) was used instead of4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g,80.4 mmol).

Synthesis Example 9-2: Preparation of Intermediate Compound Q-16

Compound Q-16 (20.3 g, yield 86%; MS:[M+H]⁺=447) was prepared in thesame manner as in Synthesis Example 4-2, except that Compound Q-13 (21.1g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 9-3: Preparation of Compound 30

Compound 30 (18.9 g, yield 69%; MS:[M+H]⁺=718) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-16 (17.0g, 38.1 mmol) instead of Compound P-6, and2-chloro-4-(3-(dibenzo[b,d]furan-1-yl)phenyl)-6-phenyl-1,3,5-triazine(16.5 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 9-4: Preparation of Compound 39

Compound 39 (17.4 g, yield 65%; MS:[M+H]⁺=704) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-16 (17.0g, 38.1 mmol) instead of Compound P-6, and2-([1,1′:3′,1″-terphenyl]-5′-yl)-4-chloro-6-phenyl-1,3,5-triazine (16.0g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 9-5: Preparation of Compound 44

Compound 44 (19.4 g, yield 62%; MS:[M+H]⁺=820) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-16 (17.0g, 38.1 mmol) instead of Compound P-6, and2-(3-chlorophenyl)-4-(4-(9,9-dimethyl-9H-fluoren-3-yl)phenyl)-6-phenyl-1,3,5-triazine(20.4 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 9-6: Preparation of Compound 63

Compound 63 (17.4 g, yield 65%; MS:[M+H]⁺=704) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-16 (17.0g, 38.1 mmol) instead of Compound P-6, and2-([1,1′:3′,1″-terphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (16.0g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 9-7: Preparation of Compound 64

Compound 64 (17.5 g, yield 64%; MS:[M+H]⁺=718) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-16 (17.0g, 38.1 mmol) instead of Compound P-6, and2-chloro-4-(3-(dibenzo[b,d]furan-4-yl)phenyl)-6-phenyl-1,3,5-triazine(16.5 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 9-8: Preparation of Compound 74

Compound 74 (17.3 g, yield 62%; MS:[M+H]⁺=734) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-16 (17.0g, 38.1 mmol) instead of Compound P-6, and2-(4-chlorophenyl)-4-(dibenzo[b,d]thiophen-2-yl)-6-phenyl-1,3,5-triazine(17.1 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 10-1: Preparation of Intermediate Compound Q-17

Compound Q-17 (28.0 g, yield 63%; MS:[M+H]⁺=551) was prepared in thesame manner as in Synthesis Example 4-1, except that 6′-chloro-1,1′:3′,1“:4”,1′″-quaterphenyl (27.4 g, 80.4 mmol) was used instead of4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g,80.4 mmol).

Synthesis Example 10-2: Preparation of Intermediate Compound Q-18

Compound Q-18 (25.9 g, yield 82%; MS:[M+H]⁺=599) was prepared in thesame manner as in Synthesis Example 4-2, except that Compound Q-17 (29.1g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 10-3: Preparation of Compound 31

Compound 31 (18.2 g, yield 68%; MS:[M+H]⁺=703) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-18 (22.8g, 38.1 mmol) instead of Compound P-6, and4-chloro-2,6-diphenylpyrimidine (10.2 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 11-1: Preparation of Intermediate Compound Q-19

Compound Q-19 (25.2 g, yield 66%; MS:[M+H]⁺=475) was prepared in thesame manner as in Synthesis Example 4-1, except that2-([1,1′:2′,1″-terphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(28.6 g, 80.4 mmol) was used instead of4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g,80.4 mmol).

Synthesis Example 11-2: Preparation of Intermediate Compound Q-20

Compound Q-20 (22.1 g, yield 80%; MS:[M+H]⁺=523) was prepared in thesame manner as in Synthesis Example 4-2, except that Compound Q-19 (25.1g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 11-3: Preparation of Compound 32

Compound 32 (15.8 g, yield 61%; MS:[M+H]⁺=678) was prepared in the samemanner as in Synthesis Example 1-1, except for using Q-20 (19.9 g, 38.1mmol) instead of Compound P-6, and2-chloro-4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazine (12.1 g, 38.1 mmol)instead of 2-bromophenanthrene.

Synthesis Example 12-1: Preparation of Compound Q-21

Compound Q-21 (27.1 g, yield 71%; MS:[M+H]⁺=475) was prepared in thesame manner as in Synthesis Example 4-1, except that[1,1′:4′,1″-terphenyl]-3-ylboronic acid (22.0 g, 80.4 mmol) was usedinstead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane(28.5 g, 80.4 mmol).

Synthesis Example 12-2: Preparation of Compound Q-22

Compound Q-22 (21.5 g, yield 78%; MS:[M+H]⁺=523) was prepared in thesame manner as in Synthesis Example 4-2, except that Compound Q-21 (25.1g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 12-3: Preparation of Compound 33

Compound 33 (18.8 g, yield 69%; MS:[M+H]⁺=718) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-22 (19.9g, 38.1 mmol) instead of Compound P-6, and2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (13.6 g,38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 12-4: Preparation of Compound 67

Compound 67 (17.2 g, yield 63%; MS:[M+H]⁺=718) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-22 (19.9g, 38.1 mmol) instead of Compound P-6, and2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (13.6 g,38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 13-1: Preparation of Intermediate Compound Q-23

Compound Q-23 (24.5 g, yield 64%; MS:[M+H]⁺=475) was prepared in thesame manner as in Synthesis Example 4-1, except that[1,1′:3′,1″-terphenyl]-3-ylboronic acid (22.0 g, 80.4 mmol) was usedinstead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane(28.5 g, 80.4 mmol).

Synthesis Example 13-2: Preparation of Intermediate Compound Q-24

Compound Q-24 (20.7 g, yield 75%; MS:[M+H]⁺=523) was prepared in thesame manner as in Synthesis Example 4-2, except that Compound Q-23 (25.1g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 13-3: Preparation of Compound 34

Compound 34 (19.6 g, yield 73%; MS:[M+H]⁺=704) was prepared in the samemanner as in Synthesis Example 4-1, except for using Q-24 (19.9 g, 38.1mmol) instead of Compound P-6, and2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (13.1 g, 38.1 mmol)instead of 2-bromophenanthrene.

Synthesis Example 13-4: Preparation of Compound 69

Compound 69 (18.8 g, yield 70%; MS:[M+H]⁺=704) was prepared in the samemanner as in Synthesis Example 1-1, except for using Q-24 (19.9 g, 38.1mmol) instead of Compound P-6, and2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (13.1 g, 38.1 mmol)instead of 2-bromophenanthrene.

Synthesis Example 14-1: Preparation of Intermediate Compound Q-25

Compound Q-25 (21.8 g, yield 68%; MS:[M+H]⁺=399) was prepared in thesame manner as in Synthesis Example 4-1, except that[1,1′-biphenyl]-3-ylboronic acid (15.9 g, 80.4 mmol) was used instead of4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g,80.4 mmol).

Synthesis Example 14-2: Preparation of Intermediate Compound Q-26

Compound Q-26 (16.5 g, yield 70%; MS:[M+H]⁺=447) was prepared in thesame manner as in Synthesis Example 4-2, except that Compound Q-25 (21.1g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 14-3: Preparation of Compound 35

Compound 35 (17.4 g, yield 65%; MS:[M+H]⁺=704) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-26 (19.9g, 38.1 mmol) instead of Compound P-6, and2-([1,1′:2′,1″-terphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (16.0g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 14-4: Preparation of Compound 71

Compound 71 (15.8 g, yield 59%; MS-[M+H]⁺=704) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-26 (19.9g, 38.1 mmol) instead of Compound P-6, and2-([1,1′-3′,1″-terphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (16.0g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 15-1: Preparation of Intermediate Compound Q-27

Compound Q-27 (27.4 g, yield 62%; MS:[M+H]⁺=549) was prepared in thesame manner as in Synthesis Example 4-1, except that(4-(triphenylen-2-yl)phenyl)boronic acid (28.0 g, 80.4 mmol) was usedinstead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane(28.5 g, 80.4 mmol).

Synthesis Example 15-2: Preparation of Intermediate Compound Q-28

Compound Q-28 (26.1 g, yield 83%; MS:[M+H]⁺=597) was prepared in thesame manner as in Synthesis Example 4-2, except that Compound Q-27 (29.0g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 15-3: Preparation of Compound 47

Compound 47 (20.2 g, yield 68%; MS:[M+H]⁺=778) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-28 (19.9g, 38.1 mmol) instead of Compound P-6, and2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (13.1 g, 38.1 mmol)instead of 2-bromophenanthrene.

Synthesis Example 16-1: Preparation of Intermediate Compound Q-29

Compound 29 (22.5 g, yield 59%; MS:[M+H]⁺=473) was prepared in the samemanner as in Synthesis Example 4-1, except that chrysen-2-ylboronic acid(21.9 g, 80.4 mmol) was used instead of4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g,80.4 mmol).

Synthesis Example 16-2: Preparation of Intermediate Compound Q-30

Compound Q-30 (23.9 g, yield 87%; MS:[M+H]⁺=521) was prepared in thesame manner as in Synthesis Example 4-2, except that Compound Q-29 (25.0g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 16-3: Preparation of Compound 51

Compound 51 (17.0 g, yield 61%; MS:[M+H]⁺=732) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-30 (19.8g, 38.1 mmol) instead of Compound P-6, and2-chloro-4-(dibenzo[b,d]thiophen-2-yl)-6-phenyl-1,3,5-triazine (14.2 g,38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 17-1: Preparation of Intermediate Compound Q-31

Compound Q-31 (22.8 g, yield 63%; MS:[M+H]⁺=449) was prepared in thesame manner as in Synthesis Example 4-1, except that(3a1,5a1-dihydropyren-1-yl)boronic acid (19.9 g, 80.4 mmol) was usedinstead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane(28.5 g, 80.4 mmol).

Synthesis Example 17-2: Preparation of Intermediate Compound Q-32

Compound Q-32 (22.3 g, yield 85%; MS:[M+H]⁺=497) was prepared in thesame manner as in Synthesis Example 4-2, except that Compound Q-31 (23.7g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 17-3: Preparation of Compound 52

Compound 52 (17.0 g, yield 62%; MS:[M+H]⁺=718) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-32 (18.9g, 38.1 mmol) instead of Compound P-6, and2-chloro-4-(9,9-dimethyl-9H-fluoren-1-yl)-6-phenyl-1,3,5-triazine (14.6g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 18-1: Preparation of Intermediate Compound Q-33

Compound Q-33 (27.3 g, yield 60%; MS:[M+H]⁺=565) was prepared in thesame manner as in Synthesis Example 4-1, except that(3-tritylphenyl)boronic acid (29.3 g, 80.4 mmol) was used instead of4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (28.5 g,80.4 mmol).

Synthesis Example 18-2: Preparation of Intermediate Compound Q-34

Compound Q-34 (28.1 g, yield 87%; MS:[M+H]⁺=613) was prepared in thesame manner as in Synthesis Example 4-2, except that Compound Q-33 (13.4g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 18-3: Preparation of Compound 56

Compound 56 (20.3 g, yield 64%; MS:[M+H]⁺=834) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-34 (23.3g, 38.1 mmol) instead of Compound P-6, and2-chloro-4-(9,9-dimethyl-9H-fluoren-4-yl)-6-phenyl-1,3,5-triazine (14.6g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 19-1: Preparation of Intermediate Compound Q-35

Compound Q-35 (21.0 g, yield 55%; MS:[M+H]⁺=475) was prepared in thesame manner as in Synthesis Example 4-1, except that[1,1′:4′,1″-terphenyl]-4-ylboronic acid (22.0 g, 80.4 mmol) was usedinstead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane(28.5 g, 80.4 mmol).

Synthesis Example 19-2: Preparation of Intermediate Compound Q-36

Compound Q-36 (24.6 g, yield 89%; MS:[M+H]⁺=523) was prepared in thesame manner as in Synthesis Example 4-2, except that Compound Q-35 (25.1g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 19-3: Preparation of Compound 75

Compound 75 (16.0 g, yield 67%; MS:[M+H]⁺=627) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound Q-36 (19.9g, 38.1 mmol) instead of Compound P-6, and4-chloro-2,6-diphenylpyrimidine (10.2 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 20: Preparation of Intermediate Compound R-6

1-Bromo-3-iodobenzene (50 g, 176.7 mmol) and 2-bromothiophenol (40.1 g,212.0 mmol) were dispersed in ethanol (EtOH, 500 ml) to which NaOH (9.2g, 229.7 mmol) was added and then refluxed for 6 hours. After completionof the reaction, the reaction solution was cooled to room temperature,and water was added thereto. The obtained organic layer was distilledunder reduced pressure. The mixture was filtered through silica gel toobtain Compound R-1 (48.6 g, yield 80%; MS: [M+H]⁺=342).

After Compound R-1 (40.0 g, 116.3 mmol) was dissolved in 500 ml ofdichloromethane (DCM), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)(31.6 g, 140.0 mmol) was added thereto and stirred at room temperaturefor 24 hours. After completion of the reaction, the mixture wasextracted three times with an excess amount of water. The organic layerwas dried over magnesium sulfate and then distilled under reducedpressure to obtain Compound R-2 (21.7 g, yield 71%; MS: [M+H]⁺=262).

After Compound R-2 (20 g, 76.0 mmol) was dissolved in tetrahydrofuran(250 ml), the temperature was lowered to −78° C. and 1.7Mtert-butyllithium (t-BuLi) (44.7 ml, 76.0 mmol) was slowly added. Afterstirring at the same temperature for one hour, triisopropylborate(B(OiPr)₃) (20.1 ml, 152.0 mmol) was added and stirred for 3 hours whilegradually raising the temperature to room temperature. To the reactionmixture was added 2N aqueous hydrochloric acid solution (100 ml) and themixture was stirred at room temperature for 1.5 hours. The resultingprecipitate was filtered, washed sequentially with water and ethylether, and dried under vacuum. After drying, the reaction mixture wasdispersed in ethyl ether, stirred for two hours, filtered and dried toobtain Compound R-3 (151 g, yield 87%; MS: [M+H]⁺=229).

After Compound R-3 (15.0 g, 65.8 mmol) and2-chloro-4,6-diphenyl-1,3,5-triazine (17.6 g, 162.3 mmol) were dispersedin tetrahydrofuran (200 ml), 2M potassium aqueous solution (aq.K₂CO₃)(98.7 ml, 197.4 mmol) was added andtetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄] (1.5 g, 2 mol %) wasadded. The mixture was stirred and refluxed for 5 hours. The temperaturewas lowered to room temperature and the resulting solid was filtered.The filtered solid was recrystallized from tetrahydrofuran and ethylacetate, filtered and then dried to obtain compound R-4 (24.1 g, yield88%; MS: [M+H]⁺=416).

Compound R-4 (40 g, 96.3 mmol) was dissolved in chloroform (350 mL) towhich acetic acid (350 mL) was added and Br₂ (5.2 mL, 101.1 mmol) wasadded dropwise at 0° C. The obtained mixture was warmed to roomtemperature and stirred for 5 hours. After completion of the reaction,the reaction solution was concentrated and recrystallized from ethanolto obtain Compound R-5 (34.3 g, yield 72%; MS: [M+H]⁺=494).

Compound R-5 (40 g, 80.9 mmol), bis(pinacolato)diboron (24.7 g, 97.1mmol), potassium acetate (33.5 g, 242.7 mmol) andtetrakis(triphenylphosphine)palladium(0) [Pd(PPh₃)₄] (1.9 g, 2 mol %)were added to tetrahydrofuran (500 ml) and refluxed for 12 hours. Aftercompletion of the reaction, the mixture was cooled to room temperature,and distilled under reduced pressure to remove the solvent. This wasdissolved in chloroform and washed three times with water. The organiclayer was separated, dried with magnesium sulfate and distilled underreduced pressure to obtain Compound R-6 (39.9 g, yield 91%; MS:[M+H]⁺=542).

Synthesis Example 20-1: Preparation of Compound 5

Compound 5 (17.9 g, yield 76%; MS:[M+H]⁺=616) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound R-6 (20.6g, 38.1 mmol) instead of Compound P-6, and 3-bromofluoranthene (10.7 g,38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 20-2: Preparation of Compound 53

Compound 53 (18.9 g, yield 69%; MS:[M+H]⁺=718) was prepared in the samemanner as in Synthesis Example 1-1, except for using Compound R-6 (20.6g, 38.1 mmol) instead of Compound P-6, and3-(6-bromonaphthalen-2-yl)phenanthrene (14.6 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 21: Preparation of Intermediate Compound S-2

Compound S-1 (68.6 g, yield 86%; MS:[M+H]⁺=492) was prepared in the samemanner as manner as in the preparation method of Compound R-4 ofSynthesis Example 20, except that2-([1,1′-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (55.8 g, 162.3mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (17.6 g,162.3 mmol).

Compound S-2 (50.5 g, yield 92%; MS:[M+H]⁺=492) was prepared in the samemanner as manner as in the preparation method of Compound R-5 ofSynthesis Example 20, except that Compound S-1 (47.3 g, 96.3 mmol) wasused instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 21-1: Preparation of Compound 78

Compound 78 (14.8 g, yield 54%; MS:[M+H]⁺=720) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundS-2 (20.6 g, 38.1 mmol) instead of Compound P-6, and[1,1′:4′,1″-terphenyl]-2′-ylboronic acid (10.4 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 22: Preparation of Intermediate Compound S-3

Compound S-3 (71.0 g, yield 89%; MS:[M+H]⁺=492) was prepared in the samemanner as manner as in the preparation method of Compound R-4 ofSynthesis Example 20, except that2-([1,1′-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (55.8 g, 162.3mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (17.6 g,162.3 mmol).

Compound S-4 (49.4 g, yield 90%; MS:[M+H]⁺=570) was prepared in the samemanner as manner as in the preparation method of Compound R-5 ofSynthesis Example 20, except that Compound S-3 (47.3 g, 96.3 mmol) wasused instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 22-1: Preparation of Compound 79

Compound 79 (20.6 g, yield 68%; MS:[M+H]⁺=796) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using S-4 (21.7g, 38.1 mmol) instead of Compound P-6, and(4′-phenyl-[1,1′:3′,1″-terphenyl]-4-yl)boronic acid (13.3 g, 38.1 mmol)instead of 2-bromophenanthrene.

Synthesis Example 23: Preparation of Intermediate Compound S-6

Compound S-5 (57.9 g, yield 86%; MS:[M+H]⁺=415) was prepared in the samemanner as manner as in the preparation method of Compound R-4 ofSynthesis Example 20, except that 2-chloro-4,6-diphenylpyrimidine (43.3g, 162.3 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine(17.6 g, 162.3 mmol).

Compound S-6 (41.3 g, yield 87%; MS:[M+H]⁺=493) was prepared in the samemanner as manner as in the preparation method of Compound R-5 ofSynthesis Example 20, except that Compound S-3 (39.9 g, 96.3 mmol) wasused instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 23-1: Preparation of Compound 43

Compound 43 (18.4 g, yield 67%; MS:[M+H]⁺=719) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using S-6 (18.8g, 38.1 mmol) instead of Compound P-6, and[1,1′:3′,1″:3″,1′″-quaterphenyl]-4-ylboronic acid (13.3 g, 38.1 mmol)instead of 2-bromophenanthrene.

Synthesis Example 23-2: Preparation of Compound 80

Compound 80 (17.8 g, yield 65%; MS:[M+H]⁺=719) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using S-6 (18.8g, 38.1 mmol) instead of Compound P-6, and[1,1′:2′,1″:4″,1′″-quaterphenyl]-4′″-ylboronic acid (13.3 g, 38.1 mmol)instead of 2-bromophenanthrene.

Synthesis Example 24: Preparation of Intermediate Compound S-8

Compound S-7 (80.5 g, yield 83%; MS:[M+H]⁺=598) was prepared in the samemanner as manner as in the preparation method of Compound R-4 ofSynthesis Example 20, except that2-(4-chlorophenyl)-4-(dibenzo[b,d]thiophen-2-yl)-6-phenyl-1,3,5-triazine(73.0 g, 162.3 mmol) was used instead of2-chloro-4,6-diphenyl-1,3,5-triazine (17.6 g, 162.3 mmol).

Compound S-8 (52.8 g, yield 81%; MS:[M+H]⁺=676) was prepared in the samemanner as manner as in the preparation method of Compound R-5 ofSynthesis Example 20, except that Compound S-7 (57.6 g, 96.3 mmol) wasused instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 24-1: Preparation of Compound 18

Compound 18 (17.5 g, yield 54%; MS:[M+H]⁺=850) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundS-8 (18.8 g, 38.1 mmol) instead of Compound P-6, and4,4,5,5-tetramethyl-2-(10-phenylphenanthren-9-yl)-1,3,2-dioxaborolane(14.5 g, 38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 25: Preparation of Intermediate Compound S-10

Compound S-9 (71.4 g, yield 87%; MS:[M+H]⁺=506) was prepared in the samemanner as manner as in the preparation method of Compound R-4 ofSynthesis Example 20, except that2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (58.1 g,162.3 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine(17.6 g, 162.3 mmol).

Compound S-10 (46.2 g, yield 82%; MS:[M+H]⁺=584) was prepared in thesame manner as manner as in the preparation method of Compound R-5 ofSynthesis Example 20, except that Compound S-9 (48.7 g, 96.3 mmol) wasused instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 25-1: Preparation of Compound 20

Compound 20 (18.7 g, yield 67%; MS:[M+H]⁺=732) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundS-10 (34.5 g, 38.1 mmol) instead of Compound P-6, andtriphenylen-2-ylboronic acid (10.4 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 26: Preparation of Intermediate Compound S-12

Compound S-11 (71.6 g, yield 89%; MS:[M+H]⁺=496) was prepared in thesame manner as manner as in the preparation method of Compound R-4 ofSynthesis Example 20, except that2-([1,1′-biphenyl]-4-yl-2′,3′,4′,5′,6′-d5)-4-chloro-6-phenylpyrimidine(56.5 g, 162.3 mmol) was used instead of2-chloro-4,6-diphenyl-1,3,5-triazine (17.6 g, 162.3 mmol).

Compound S-12 (47.0 g, yield 85%; MS:[M+H]⁺=574) was prepared in thesame manner as manner as in the preparation method of Compound R-5 ofSynthesis Example 20, except that Compound S-11 (47.7 g, 96.3 mmol) wasused instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 26-1: Preparation of Compound 24

Compound 24 (19.5 g, yield 71%; MS:[M+H]⁺=722) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundS-12 (21.9 g, 38.1 mmol) instead of Compound P-6, andtriphenylen-2-ylboronic acid (10.4 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 27-1: Preparation of Intermediate Compound Q-37

Compound Q-37 (30.6 g, yield 60%; MS:[M+H]⁺=581) was prepared in thesame manner as manner as in Synthesis Example 4-1, except that(3-(triphenylsilyl)phenyl)boronic acid (30.6 g, 80.4 mmol) was usedinstead of 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane(28.5 g, 80.4 mmol).

Synthesis Example 27-2: Preparation of Intermediate Compound Q-38

Compound Q-38 (28.5 g, yield 86%; MS:[M+H]⁺=629) was prepared in thesame manner as in Synthesis Example 4-2, except that Compound Q-37 (30.7g, 52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Synthesis Example 27-3: Preparation of Compound 38

Compound 38 (19.2 g, yield 60%; MS:[M+H]⁺=840) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using Q-38(24.0 g, 38.1 mmol) instead of Compound P-6, and2-chloro-4-(dibenzo[b,d]thiophen-2-yl)-6-phenyl-1,3,5-triazine (14.2 g,38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 28: Preparation of Intermediate Compound S-14

Compound S-13 (71.4 g, yield 87%; MS:[M+H]⁺=506) was prepared in thesame manner as manner as in the preparation method of Compound R-4 ofSynthesis Example 20, except that2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (58.1 g,162.3 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine(17.6 g, 162.3 mmol).

Compound S-14 (50.1 g, yield 89%; MS:[M+H]⁺=584) was prepared in thesame manner as manner as in the preparation method of Compound R-5 ofSynthesis Example 20, except that Compound S-13 (48.7 g, 96.3 mmol) wasused instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 28-1: Preparation of Compound 41

Compound 41 (19.3 g, yield 69%; MS:[M+H]⁺=734) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundS-14 (21.9 g, 38.1 mmol) instead of Compound P-6, and[1,1′:2′,1″-terphenyl]-3-ylboronic acid (10.4 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 29: Preparation of Intermediate Compound S-16

Compound S-15 (78.7 g, yield 93%; MS:[M+H]⁺=522) was prepared in thesame manner as manner as in the preparation method of Compound R-4 ofSynthesis Example 20, except that2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine (60.7 g,162.3 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine(17.6 g, 162.3 mmol).

Compound S-16 (50.3 g, yield 87%; MS:[M+H]⁺=600) was prepared in thesame manner as manner as in the preparation method of Compound R-5 ofSynthesis Example 20, except that Compound S-15 (50.2 g, 96.3 mmol) wasused instead of Compound R-4 (40 g, 96.3 mmol).

Synthesis Example 29-1: Preparation of Compound 42

Compound 42 (20.6 g, yield 72%; MS:[M+H]⁺=750) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundS-16 (22.9 g, 38.1 mmol) instead of Compound P-6, and[1,1′:3′,1″-terphenyl]-3-ylboronic acid (10.4 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 30: Preparation of Compound 23

After Compound 6 (20 g, 28.5 mmol) was dissolved in tetrahydrofuran (500ml), the temperature was lowered to −78° C. and 1.7 M tert-butyllithium(t-BuLi) (16.8 ml, 28.5 mmol) was slowly added thereto. After stirringat the same temperature for one hour, excess D₂O was added dropwise toterminate the reaction. The temperature is gradually increased to roomtemperature, the organic layer was separated, dried with magnesiumsulfate and distilled under reduced pressure. The obtained mixture waspurified by column chromatography with hexane/ethyl acetate (10:1) toobtain Compound 23 (9.6 g, yield 48%; MS: [M+H]⁺=703)

Synthesis Example 31: Preparation of Compound 60

Compound 60 (8.6 g, yield 42%; MS:[M+H]⁺=718) was prepared in the samemanner as manner as in Synthesis Example 30, except that Compound 8(20.4 g, 28.5 mmol) and 1.7M tert-butyllithium (t-BuLi) (33.5 ml, 57.0mmol) were used instead of Compound P-6.

Synthesis Example 32-1: Preparation of Intermediate Compound Q-39

Compound Q-39 (22.0 g, yield 82%; MS:[M+H]⁺=704) was prepared in thesame manner as manner as in Synthesis Example 1-1, except for usingCompound Q-36 (19.9 g, 38.1 mmol) instead of Compound P-6, and2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (13.1 g, 38.1 mmol)instead of 2-bromophenanthrene.

Synthesis Example 32-2: Preparation of Compound 73

Compound 73 (9.9 g yield 49%; MS:[M+H]⁺=705) was prepared in the samemanner as manner as in Synthesis Example 30, except that Compound Q-39(20.1 g, 28.5 mmol) was used instead of Compound 6.

Synthesis Example 33: Preparation of Intermediate Compound T-7

Compound T-1 (65.3 g, yield 62%; MS:[M+H]⁺=314) was prepared in the samemanner as manner as in the preparation method of Compound P-1 ofSynthesis Example 1, except that (4-chloro-2-methoxyphenyl)boronicacid)(62.2 g, 333.5 mmol) was used instead of(5-chloro-2-methoxyphenyl)boronic acid) (62.2 g, 333.5 mmol).

Compound T-2 (43.0 g, yield 90%; MS:[M+H]⁺=300) was prepared in the samemanner as manner as in the preparation method of Compound P-2 ofSynthesis Example 1, except that Compound T-1 (50.0 g, 158.5 mmol) wasused instead of Compound P-1 (50.0 g, 158.5 mmol).

Compound T-3 (30.6 g, yield 82%; MS:[M+H]⁺=280) was prepared in the samemanner as manner as in the preparation method of Compound P-3 ofSynthesis Example 1, except that Compound T-2 (40.0 g, 132.7 mmol) wasused instead of Compound P-2 (40.0 g, 132.7 mmol).

Compound T-4 (25.0 g, yield 95%; MS:[M+H]⁺=247) was prepared in the samemanner as manner as in the preparation method of Compound P-4 ofSynthesis Example 1, except that Compound T-3 (30.0 g, 106.6 mmol) wasused instead of Compound P-3 (30.0 g, 106.6 mmol).

Compound T-5 (31.7 g, yield 90%; MS:[M+H]⁺=434) was prepared in the samemanner as manner as in the preparation method of Compound P-5 ofSynthesis Example 1, except that Compound T-4 (20.0 g, 81.2 mmol) wasused instead of Compound P-4 (20.0 g, 81.2 mmol).

Compound T-6 (37.1 g, yield 83%; MS:[M+H]⁺=550) was prepared in the samemanner as manner as in the preparation method of Compound P-5 ofSynthesis Example 1, except for using Compound T-4 (20.0 g, 81.2 mmol)instead of Compound P-4 (20.0 g, 81.2 mmol), and2-chloro-4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenyl-1,3,5-triazine (31.1g, 81.2 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

Compound T-7 (29.4 g, yield 71%; MS:[M+H]⁺=510) was prepared in the samemanner as manner as in the preparation method of Compound P-5 ofSynthesis Example 1, except for using Compound T-4 (20.0 g, 81.2 mmol)instead of Compound P-4 (20.0 g, 81.2 mmol), and2-(2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (27.9 g, 81.2 mmol)instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

Synthesis Example 33-1: Preparation of Compound 76

Compound 76 (23.9 g, yield 89%; MS:[M+H]⁺=704) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundT-5 (16.5 g, 38.1 mmol) instead of Compound P-6, and[1,1′:3′,1″:4″,1′″-quaterphenyl]-4-ylboronic acid (13.3 g, 38.1 mmol)instead of 2-bromophenanthrene.

Synthesis Example 33-2: Preparation of Compound 40

Compound 40 (26.6 g, yield 82%; MS:[M+H]⁺=850) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundT-6 (21.0 g, 38.1 mmol) instead of Compound P-6, and4-(triphenylsilyl)phenyl)boronic acid (14.5 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 33-3: Preparation of Compound 21

Compound 21 (22.1 g, yield 86%; MS:[M+H]⁺=676) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundT-7 (19.4 g, 38.1 mmol) instead of Compound P-6, andfluoranthen-3-ylboronic acid (9.4 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 34: Preparation of Intermediate Compound U-8

After 1,3-dibromo-2-methoxybenzene (113.2 g, 426.4 mmol) was dissolvedin tetrahydrofuran (1000 ml), the temperature was lowered to −78° C. and17M tert-butyl lithium (t-BuLi) (251.7 ml, 426.4 mmol) was slowly added.After stirring at the same temperature for one hour, triisopropyl borate(B(OiPr)₃) (113.2 ml, 852.4 mmol) was added and stirred for 3 hourswhile gradually raising the temperature to room temperature. To thereaction mixture was added 2N aqueous hydrochloric acid solution (800ml) and the mixture was stirred at room temperature for 1.5 hours. Theresulting precipitate was filtered, washed sequentially with water andethyl ether, and dried under vacuum. After drying, the residue wasrecrystallized from chloroform and ethyl acetate and dried to obtain(3-bromo-2-methoxyphenyl)boronic acid (89.6 g, yield 91%; MS:[M+H]=230).

Compound U-1 (55.8 g, yield 53%; MS:[M+H]⁺=314) was prepared in the samemanner as manner as in the preparation method of Compound P-1 ofSynthesis Example 1, except for using 1-chloro-3-fluoro-2-iodobenzene(85.5 g, 333.5 mmol) instead of 1-bromo-3-fluoro-2-iodobenzene, and(3-bromo-2-methoxyphenyl)boronic acid (77.0 g, 333.5 mmol) instead of(5-chloro-2-methoxyphenyl)boronic acid.

Compound U-2 (39.7 g, yield 83%; MS:[M+H]⁺=300) was prepared in the samemanner as manner as in the preparation method of Compound P-2 ofSynthesis Example 1, except that Compound U-1 (50.0 g, 158.5 mmol) wasused instead of Compound P-1 (50.0 g, 158.5 mmol).

Compound U-3 (31.4 g, yield 84%; MS:[M+H]⁺=280) was prepared in the samemanner as manner as in the preparation method of Compound P-3 ofSynthesis Example 1, except that Compound U-2 (40.0 g, 132.7 mmol) wasused instead of Compound P-2 (40.0 g, 132.7 mmol).

Compound U-4 (25.5 g, yield 97%; MS:[M+H]⁺=247) was prepared in the samemanner as manner as in the preparation method of Compound P-4 ofSynthesis Example 1, except that Compound U-3 (30.0 g, 106.6 mmol) wasused instead of Compound P-3 (30.0 g, 106.6 mmol).

Compound U-5 (31.1 g, yield 86%; MS:[M+H]⁺=445) was prepared in the samemanner as manner as in the preparation method of Compound P-5 ofSynthesis Example 1, except for using Compound U-4 (20.0 g, 81.2 mmol)instead of Compound P-4 (20.0 g, 81.2 mmol), and triphenylen-2-ylboronicacid (22.1 g, 81.2 mmol) instead of2-chloro-4,6-diphenyl-1,3,5-triazine.

Compound U-6 (24.7 g, yield 90%; MS:[M+H]⁺=521) was prepared in the samemanner as in Synthesis Example 4-2, except that Compound U-5 (22.6 g,52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Compound U-7 (30.8 g, yield 88%; MS:[M+H]⁺=431) was prepared in the samemanner as manner as in the preparation method of Compound P-5 ofSynthesis Example 1, except for using Compound U-4 (20.0 g, 81.2 mmol)instead of Compound P-4, and [1,1′:4′,1″-terphenyl]-4-ylboronic acid(22.3 g, 81.2 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

Compound U-8 (24.3 g, yield 88%; MS:[M+H]⁺=523) was prepared in the samemanner as in Synthesis Example 4-2, except that Compound U-7 (22.8 g,52.8 mmol) was used instead of Compound Q-5.

Synthesis Example 34-1: Preparation of Compound 22

Compound 22 Compound 22 (35.4 g, yield 93%; MS:[M+H]⁺=702) was preparedin the same manner as manner as in Synthesis Example 1-1, except forusing Compound U-6 (19.8 g, 38.1 mmol) instead of Compound P-6, and2-([1,1′-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (13.1 g, 38.1mmol) instead of 2-bromophenanthrene.

Synthesis Example 34-2: Preparation of Compound 77

Compound 77 (24.9 g, yield 91%; MS:[M+H]⁺=718) was prepared in SynthesisExample 1-1, except for using Compound U-8 (19.9 g, 38.1 mmol) insteadof Compound P-6, and2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine (13.6 g,38.1 mmol) instead of 2-bromophenanthrene.

Synthesis Example 35: Preparation of Intermediate Compound W-8

After 2-bromo-1,3-dimethoxybenzene (92.6 g, 426.4 mmol) was dissolved intetrahydrofuran (1000 ml), the temperature was lowered to −78° C. and1.7M tert-butyl lithium (t-BuLi) (251.7 ml, 426.4 mmol) was slowlyadded. After stirring at the same temperature for 1 hour,triisopropylborate (B(OiPr)₃) (113.2 ml, 852.4 mmol) was added and themixture was stirred for 3 hours while gradually raising the temperatureto room temperature. To the reaction mixture was added 2N aqueoushydrochloric acid solution (800 ml) and the mixture was stirred at roomtemperature for 1.5 hours. The resulting precipitate was filtered,washed sequentially with water and ethyl ether, and dried under vacuum.After drying, the reaction product was recrystallized from chloroformand ethyl acetate and dried to obtain (2,6-dimethoxyphenyl)boronic acid(63.6 g, yield 82%; MS: [M+H]⁺=183).

Compound W-1 (35.6 g, yield 40%; MS:[M+H]⁺=267) was prepared in the samemanner as manner as in the preparation method of Compound P-1 ofSynthesis Example 1, except for using 1-chloro-3-fluoro-2-iodobenzene(85.5 g, 333.5 mmol) instead of 1-bromo-3-fluoro-2-iodobenzene, and(2,6-dimethoxyphenyl)boronic acid (60.7 g, 333.5 mmol) instead of(5-chloro-2-methoxyphenyl)boronic acid.

Compound W-2 (33.3 g, yield 88%; MS:[M+H]⁺=239) was prepared in the samemanner as manner as in the preparation method of Compound P-2 ofSynthesis Example 1, except that Compound W-1 (42.3 g, 158.5 mmol) wasused instead of Compound P-1 (50.0 g, 158.5 mmol), and boron tribromide(31.6 ml, 332.9 mmol) was used.

Compound W-3 (23.5 g, yield 81%; MS:[M+H]⁺=219) was prepared in the samemanner as manner as in the preparation method of Compound P-3 ofSynthesis Example 1, except that Compound W-2 (31.7 g, 132.7 mmol) wasused instead of Compound P-2 (40.0 g, 132.7 mmol).

After Compound W-3 (20.0 g, 91.5 mmol) was dispersed in acetonitrile(250 ml), calcium carbonate (51.2 g, 109.8 mmol) andnonafluorobutanesulfonyl fluoride (41.6 g, 137.3 mmol) were addedthereto. The mixture was stirred at 80° C. for 1 hour. The reactionmixture was cooled to room temperature, filtered, washed with ethanoland water, and then dried to obtain Compound W-4 (38.9 g, yield 85%; MS:[M+H]⁺=500).

Compound W-5 (21.6 g, yield 62%; MS:[M+H]⁺=429) was prepared in the samemanner as manner as in the preparation method of Compound P-5 ofSynthesis Example 1, except for using Compound W-4 (40.7 g, 81.2 mmol)instead of Compound P-4, and triphenylen-2-ylboronic acid (22.1 g, 81.2mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

Compound W-6 (23.4 g, yield 85%; MS:[M+H]⁺=521) was prepared in the samemanner as in Synthesis Example 4-2, except that Compound W-5 (22.6 g,52.8 mmol) was used instead of Compound Q-5.

Compound W-7 (22.0 g, yield 63%; MS:[M+H]⁺=431) was prepared in the samemanner as manner as in the preparation method of Compound P-5 ofSynthesis Example 1, except for using Compound W-4 (40.7 g, 81.2 mmol)instead of Compound P-4, and [1,1′:4′,1″-terphenyl]-3-ylboronic acid(22.3 g, 81.2 mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

Compound W-8 (22.1 g, yield 80%; MS:[M+H]⁺=523) was prepared in the samemanner as in Synthesis Example 4-2, except that Compound W-7 (22.8 g,52.8 mmol) was used instead of Compound Q-5.

Synthesis Example 35-1: Preparation of Compound 16

Compound 16 (19.5 g, yield 73%; MS:[M+H]⁺=702) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundW-6 (19.8 g, 38.1 mmol) instead of Compound P-6, and2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (13.1 g, 38.1 mmol)instead of 2-bromophenanthrene.

Synthesis Example 35-2: Preparation of Compound 37

Compound 37 (15.5 g, yield 65%; MS:[M+H]⁺=628) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundW-8 (19.9 g, 38.1 mmol) instead of Compound P-6, and2-chloro-4,6-diphenyl-1,3,5-triazine (10.2 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 36: Preparation of Compound A

After 50 g (23.0 mmol) of 2-chlorodibenzothiophene was diluted with 300mL of chloroform, 18 mL (0.34 mol) of bromine was slowly added andstirred at room temperature for 12 hours. After completion of thereaction, the precipitated solid was filtered, dissolved again in excesschloroform by heating, and then washed with 20% sodium thiosulfateaqueous solution, and the organic layer was separated. This was washedagain with a saturated aqueous sodium hydrogen carbonate solution, theorganic layer was separated, water was dried with anhydrous magnesiumsulfate, and concentrated under reduced pressure. To the concentratedcompound was added 300 mL of ethyl acetate, and the mixture was stirredunder reflux. The resulting slurry was cooled at room temperature,filtered, and then dried under nitrogen to obtain a light brown compoundX-1 (32 g, yield 47%; MS: [M+H]⁺=296).

After 48 g (0.16 mol) of Compound X-1 was dissolved in 500 mL of1,4-dioxane, 49 g (0.19 mol) of bis(pinacolato)diboron was addedthereto. 31.4 g (0.32 mol) of potassium acetate was then added withstirring, and the mixture was heated to reflux. Under stirring andreflux, 2.7 g (0.005 mol) of dibenzylidene acetone palladium and 2.7 g(0.01 mol) of tricyclohexylphosphine were added, and the mixture wasstirred under reflux for 12 hours. After completion of the reaction, thereactant was cooled to room temperature, washed with water, andextracted twice with chloroform. The collected organic layer was washedonce with water, and water was removed with anhydrous magnesium sulfate,followed by filtration and concentration. The concentrate was heatedunder stirring with a small amount of ethyl acetate and an excess ofhexane mixed solution and filtered to obtain a white compound X-2 (43 g,yield 78%; MS [M+H]⁺=345).

10 g (0.03 mol) of Compound X-2 and 8.4 g (0.03 mol) of2-chloro-4,6-diphenyl-1,3,5-triazine were dissolved in 100 mL of1,4-dioxane to which K₃PO₄ 19 g (0.09 mol) was added and the mixture wasstirred under reflux. To this mixture were added 570 mg (0.001 mol) ofdibenzylideneacetone palladium and 560 mg (0.002 mol) oftricyclohexylphosphine, and the mixture was stirred under reflux for 12hours. After completion of the reaction, the reactant was cooled to roomtemperature, washed with water, extracted twice with ethyl acetate,water was removed with anhydrous magnesium sulfate, filtered, andconcentrated under reduced pressure so that a small amount of ethylacetate remained. An excess amount of acetone was added to theconcentrated compound, slurried and then filtered to obtain a whitecompound X-3 (11 g, yield 83%; MS: [M+H]⁺=150).

10 g (0.022 mol) of Compound 1-3 and 6.0 g (0.022 mol) oftriphenylen-2-ylboronic acid were diluted in 80 mL of 1,4-dioxane, and13.9 g (0.066 mol) of K₃PO₄ was added to the mixed solution, followed byheating, and the mixture was stirred under reflux. To this mixture wasadded 380 mg (0.66 mmol) of dibenzylideneacetone palladium and 370 mg(1.3 mmol) of tricyclohexylphosphine and stirred under reflux for 12hours. After completion of the reaction, the reactant was cooled to roomtemperature, and the precipitated solid was filtered, dissolved inchloroform, and washed twice with water. The collected organic layer wasdried over anhydrous magnesium sulfate, filtered and purified byrecrystallization using chloroform and ethyl acetate as a mixed solutionto obtain a white Compound A (9.6 g, yield 68%; MS: [M+H]⁺=642).

Synthesis Example 37: Preparation of Compound B

Compound B (35.5 g, yield 92%; MS:[M+H]⁺=476) was prepared in the samemanner as manner as in the preparation method of Compound P-5 ofSynthesis Example 1, except for using Compound Q-3 (20.1 g, 81.2 mmol)instead of Compound P-4, and(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)boronic acid (28.7 g, 81.2mmol) instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

Synthesis Example 38: Preparation of Compound C

After 4,6-dibromodibenzofuran (20 g, 61.4 mmol), and[1,1′:4′,1″-terphenyl]-3-ylboronic acid (17.6 g, 61.4 mmol) weredispersed in tetrahydrofuran (400 ml), 2M potassium carbonate aqueoussolution (aq. K₂CO₃) (92.1 ml, 184.2 mmol) was added andtetrakis(triphenylphosphine)palladium [Pd(PPh₃)₄] (1.4 g, 2 mol %) wasadded, and the mixture was stirred under reflux. After lowering thetemperature to room temperature, the mixture was extracted with waterand toluene, and the organic layer was dried with magnesium sulfate(MgSO₄) and then distilled under reduced pressure. The resulting mixturewas purified by column chromatography on silica gel with hexane: ethylacetate (15:1) to obtain Compound X-4 (54.3 g, yield 62%; MS:[M+H]⁺=475).

Compound X-5 (25.4 g, yield 92%; MS:[M+H]⁺=523) was prepared in the samemanner as in Synthesis Example 4-2, except that Compound X-4 (25.1 g,52.8 mmol) was used instead of Compound Q-5 (25.0 g, 52.8 mmol).

Compound C (19.9 g, yield 83%; MS:[M+H]⁺=628) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundX-5 (19.9 g, 38.1 mmol) instead of Compound P-6, and2-chloro-4,6-diphenyl-1,3,5-triazine (10.2 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 39: Preparation of Compound D

Dibenzo[b,d]furan-4-ylboronic acid (21.2 g, yield 94%; MS:[M+H]⁺=213)was prepared in the same manner as manner as in the preparation methodof Compound P-4 of Synthesis Example 1, except that4-bromodibenzo[b,d]furan (26.3 g, 106.6 mmol) was used instead ofCompound P-3.

Compound X-6 (25.3 g, yield 89%; MS:[M+H]⁺=351) was prepared in the samemanner as manner as in the preparation method of Compound P-5 ofSynthesis Example 1, except for using 4-bromodibenzo[b,d]thiophene (21.4g, 81.2 mmol) instead of Compound P-4, and dibenzo[b,d]furan-4-ylboronicacid (17.2 g, 81.2 mmol) instead of2-chloro-4,6-diphenyl-1,3,5-triazine.

A mixture was prepared in the same manner as manner as in thepreparation method of Compound P-5 of Synthesis Example 20, except forusing Compound X-6 (25.0 g, 71.3 mmol), chloroform (200 ml), acetic acid(200 ml) and Br₂ (3.8 mL, 74.9 mmol) instead of Compound R-4, and thenpurified by column chromatography on silica gel with hexane: ethylacetate (10:1) to obtain Compound X-7 (14.4 g, yield 47%; MS:[M+H]⁺=428).

Compound X-8 (23.9 g, yield 95%; MS:[M+H]⁺=477) was prepared in the samemanner as in Synthesis Example 4-2, except that Compound X-7 (22.7 g,52.8 mmol) was used instead of Compound Q-5.

Compound D (19.7 g, yield 89%; MS:[M+H]⁺=582) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundX-8 (18.2 g, 38.1 mmol) instead of Compound Q-5, and2-chloro-4,6-diphenyl-1,3,5-triazine (10.2 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 40: Preparation of Compound E

Compound X-9 (56.3 g, yield 87%; MS:[M+H]⁺=280) was prepared in the samemanner as manner as in the preparation method of Compound X-1 ofSynthesis Example 36, except that 2-chlorodibenzofuran (46.6 g, 230.0mmol) was used instead of 2-chlorodibenzothiophene.

Compound X-10 (21.7 g, yield 96%; MS:[M+H]⁺=279) was prepared in thesame manner as manner as in the preparation method of Compound P-5 ofSynthesis Example 1, except for using Compound X-9 (22.9 g, 81.2 mmol)instead of Compound P-4, and phenylboronic acid (17.3 g, 81.2 mmol)instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

Compound E (15.6 g, yield 87%; MS:[M+H]⁺=471) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundX-10 (10.6 g, 38.1 mmol) instead of Compound P-6, andtriphenylen-2-ylboronic acid (10.4 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 41: Preparation of Compound F

Compound X-11 (29.0 g, yield 89%; MS:[M+H]⁺=400) was prepared in thesame manner as manner as in the preparation method of Compound P-5 ofSynthesis Example 1, except for using dibenzo[b,d]furan-4-ylboronic acid(17.2 g, 81.2 mmol) instead of Compound P-4, and2-chloro-4,6-diphenyl-1,3,5-triazine (21.7 g, 81.2 mmol) instead of2-chloro-4,6-diphenyl-1,3,5-triazine.

A mixture was obtained in the same manner as manner as in thepreparation method of Compound R-5 of Synthesis Example 20, except forusing Compound X-12 (28.5 g, 71.3 mmol), chloroform (200 ml), aceticacid (200 ml) and Br₂ (3.8 mL, 74.9 mmol) instead of Compound R-4, andthen purified by column chromatography on silica gel with hexane: ethylacetate (10:1) to obtain Compound X-12 (23.5 g, yield 69%; MS:[M+H]⁺=478).

Compound F (21.7 g, yield 91%; MS:[M+H]⁺=626) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundX-12 (18.2 g, 38.1 mmol) instead of Compound P-6, andtriphenylen-2-ylboronic acid (10.4 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 42: Preparation of Compound G

Compound G (19.8 g, yield 94%; MS:[M+H]⁺=552) was prepared in the samemanner as manner as in Synthesis Example 1-1, except for using CompoundX-12 (18.2 g, 38.1 mmol) instead of Compound P-6, and[1,1′-biphenyl]-4-ylboronic acid (7.5 g, 38.1 mmol) instead of2-bromophenanthrene.

Synthesis Example 43: Preparation of Compound H

Compound H (16.2 g, yield 72%; MS:[M+H]⁺=560) was prepared in the samemanner as manner as in Synthesis Example 1-1, except that2-bromo-9,9-dimethyl-9H-fluorene (10.4 g, 38.1 mmol) was used instead of2-bromophenanthrene.

Example 1

A glass substrate on which a thin film of ITO (indium tin oxide) wascoated in a thickness of 1,300 Å was put into distilled water containingthe detergent dissolved therein and washed by the ultrasonic wave. Theused detergent was a product commercially available from Fisher Co. andthe distilled water was one which had been twice filtered by using afilter commercially available from Millipore Co. The ITO was washed for30 minutes, and washing with ultrasonic waves was then repeated twicefor 10 minutes by using distilled water. After the washing withdistilled water was completed, the substrate was ultrasonically washedwith isopropyl alcohol, acetone, and methanol solvent, and dried, afterwhich it was transported to a plasma cleaner. Then, the substrate wascleaned with oxygen plasma for 5 minutes, and then transferred to avacuum evaporator.

On the ITO transparent electrode thus prepared, a compound of HI-1 asdescribed below was thermally deposited under vacuum to a thicknesses of50 Å to form the hole injection layer.

On the hole injection layer, the compound of HT-1 was thermallydeposited under vacuum to a thicknesses of 250 Å to form a holetransport layer, and a compound of HT-2 was deposited under vacuum to athickness of 50 Å on the HT-1 deposition layer to form an electronblocking layer.

Next, on the HT-2 vapor deposition layer, the compound 1 prepared inSynthesis Example 1-1 was co-deposited with 12% by weight of aphosphorescent dopant YGD-1 to form a light emitting layer having athickness of 400 Å.

On the light emitting layer, a material of ET-1 was deposited undervacuum to a thickness of 250 Å, and additionally a material of ET-2 wasco-deposited with 2% by weight of L₁ to a thickness of 100 Å to form anelectron transport layer and an electron injection layer. Aluminum wasdeposited on the electron injection layer to a thickness of 1000 Å toform a cathode.

In the above process, the vapor deposition rate of the organic materialwas maintained at 0.4 to 0.7 Å/sec, the deposition rate of aluminum wasmaintained at 2 Å/sec, and the degree of vacuum during vapor depositionwas maintained at 2×10⁻⁷˜5×10⁻⁶ torr.

Examples 2 to 49

The organic light emitting devices of Examples 2 to 49 were eachfabricated in the same manner as in Example 1, except that thephosphorescent host material and the dopant content at the time offorming the light emitting layer were changed as shown in Tables 1 to 3below.

Comparative Examples 1 to 10

The organic light emitting devices of Comparative Examples 1 to 10 wereeach fabricated in the same manner as in Example 1, except that thephosphorescent host material and the dopant content at the time offorming the light emitting layer were changed as shown in Table 3 below.Here, the host materials represented by compound A to compound I used inComparative Examples are as follows.

Experimental Example 1

After an electric current was applied to each of the organic lightemitting devices fabricated in Examples 1 to 49 and Comparative Examples1 to 10, the voltage, efficiency, luminance, color coordinate and lifetime were measured, and the results are shown in Tables 1 to 3 below. Inthis case, T95 means the time required for the luminance to be reducedto 95% when the initial luminance at a light density of 50 mA/cm² wastaken as 100%.

TABLE 1 Host: dopant Voltage(V) Efficiency Color Life time (thickness,Å) (@ 10 mA/ (Cd/A) coordinate (T₉₅, h) No. dopant content cm²) (@10mA/cm²) (x, y) (@50 mA/cm²) Example compound 1: 2.99 62.8 (0.46, 0.54)47.5  1 YGD-1 (400)12% Example compound 2: 2.99 64.1 (0.46, 0.53) 50.5 2 YGD-1(400)12% Example compound 3: 2.97 65.0 (0.46, 0.52) 47.0  3YGD-1(400)16% Example compound 4: 3.15 62.8 (0.46, 0.53) 78.6  4 YGD-1(400)12% Example compound 5: 3.11 53.8 (0.47, 0.52) 46.4  5YGD-1(400)14% Example compound 6: 3.23 62.7 (0.47, 0.53) 49.9  6YGD-1(400)12% Example compound 7: 3.20 63.1 (0.46, 0.53) 50.3  7YGD-1(400)12% Example compound 8: 3.30 55.7 (0.47, 0.52) 87.9  8YGD-1(400)16% Example compound 9: 2.97 64.2 (0.46, 0.54) 70.5  9YGD-1(400)16% Example compound 10: 3.12 60.3 (0.47, 0.53) 47.7 10YGD-1(400)16% Example compound 11: 2.89 63.0 (0.46, 0.53) 69.8 11YGD-1(400)16% Example compound 14: 3.08 56.1 (0.45, 0.54) 47.6 12YGD-1(400)16% Example compound 15: 3.00 63.0 (0.46, 0.53) 47.1 13YGD-1(400)12% Example compound 16: 3.28 63.2 (0.46, 0.53) 41.8 14YGD-1(400)12% Example compound 12: 3.55 65.9 (0.46, 0.52) 126.2 15YGD-1(200:200)16% Example compound 13: 3.51 67.2 (0.46, 0.53) 116.0 16PH-1:YGD-1(160:240)16% Example compound 4: PH- 3.57 67.7 (0.46, 0.53)191.9 17 2:YGD-1(160:240)12% Example compound 17: 3.53 67.8 (0.47, 0.53)125.1 18 PH-2:YGD-1(200:200)16% Example compound 18: 3.56 70.2 (0.45,0.53) 132.8 19 PH-2:YGD-1(160:240)12% Example compound 19: 3.50 68.9(0.46, 0.53) 352.0 20 PH-2:YGD-1(200:200)15%

TABLE 2 Host: dopant Voltage(V) Efficiency Color Life time (thickness,Å) (@ 10 mA/ (Cd/A) coordinate (T₉₅, h) No. dopant content cm²) (@ 10mA/cm²) (x, y) (@50 mA/cm²) Example compound 20: 3.64 65.4 (0.45, 0.54)155.7 21 PH-3:YGD-1(160:240)12% Example compound 21: 3.58 64.1 (0.46,0.54) 100.3 22 PH-2:YGD-1(200:200)14% Example compound 22: 3.60 66.5(0.46, 0.54) 115.6 23 PH-3:YGD-1(200:200)16% Example compound 23: 3.7166.8 (0.46, 0.53) 180.3 24 PH-2:YGD-1(160:240)12% Example compound 24:3.48 67.1 (0.46, 0.53) 230.7 25 PH-2:YGD-1(160:240)12% Example compound25: 3.12 60.3 (0.46, 0.52) 48.3 26 YGD-1 (400)16% Example compound 26:3.01 61.7 (0.48, 0.51) 84.9 27 YGD-1 (400)12% Example compound 27: 2.9858.5 (0.48, 0.51) 76.1 28 YGD-1 (400)16% Example compound 28: 3.00 67.1(0.47, 0.52) 87.2 29 YGD-1 (400)16% Example compound 29: 3.04 65.4(0.46, 0.53) 68.1 30 YGD-1(400)16% Example compound 30: 3.01 66.1 (0.46,0.52) 73.6 31 YGD-1(400)16% Example compound 31: 3.12 60.2 (0.46, 0.53)77.2 32 YGD-1(400)12% Example compound 32: 3.08 64.2 (0.45, 0.53) 76.833 YGD-1(400)12% Example compound 33: 3.11 52.6 (0.45, 0.53) 46.2 34YGD-1(400)16% Example compound 34: 2.97 59.9 (0.46, 0.54) 74.3 35YGD-1(400)16% Example compound 35: 3.04 62.4 (0.45, 0.53) 79.8 36YGD-1(400)12% Example compound 36: 3.10 59.15 (0.45, 0.55) 48.4 37YGD-1(400)16% Example compound 37: 3.01 59.2 (0.45, 0.53) 44.1 38YGD-1(400)14% Example compound 38: 3.52 67.2 (0.46, 0.53) 160.3 39PH-1:YGD-1(200:200)12% Example compound 39: 3.49 72.4 (0.45, 0.54) 265.840 PH-2:YGD-1(160:240)16%

TABLE 3 Host: dopant Voltage(V) Efficiency Color Life time (thickness,Å) (@ 10 mA/ (Cd/A) coordinate (T₉₅, h) No. dopant content cm²) (@ 10mA/cm²) (x, y) (@50 mA/cm²) Example compound 40: 3.61 62.6 (0.44, 0.54)102.8 41 PH-3:YGD-1 (200:200)16% Example compound 41: 3.48 65.1 (0.47,0.53) 272.1 42 PH-2:YGD-1(160:240)16% Example compound 42: 3.52 67.7(0.45, 0.54) 326.1 43 PH-2:YGD-1(160:240)12% Example compound 43: 3.5562.4 (0.45, 0.53) 239.8 44 PH-3:YGD-1(160:240)12% Example compound 44:3.60 60.0 (0.46, 0.52) 154.2 45 PH-3:YGD-1(200:200)16% Example compound46: 3.62 64.68 (0.45, 0.53) 175.3 46 PH-1:YGD-1(160:240)16% Examplecompound 28: 3.51 67.9 (0.45, 0.54) 330.2 47 PH-2:YGD-1(160:240)16%Example compound 81: 3.53 65.3 (0.47, 0.54) 289.6 48PH-2:YGD-1(160:240)12% Example compound 45: 3.50 68.1 (0.45, 0.52) 349.849 PH-2:YGD-1(160:240)12% Comparative compound A: 3.21 61.9 (0.46, 0.53)25.9 Example 1 YGD-1(400)12% Comparative compound B: 3.17 56.2 (0.47,0.52) 27.3 Example 2 YGD-1(400)12% Comparative compound C: 2.92 62.2(0.48, 0.50) 20.3 Example 3 YGD-1(400)12% Comparative compound D: 3.1167.3 (0.48, 0.53) 26.2 Example 4 YGD-1(400)12% Comparative compound E:4.73 28.11 (0.47, 0.51) 22.2 Example 5 YGD-1(400)12% Comparativecompound F: 3.15 53.2 (0.48, 0.50) 27.5 Example 6 YGD-1(400)12%Comparative compound G: 3.14 52.7 (0.49, 0.50) 26.9 Example 7YGD-1(400)12% Comparative compound H: 3.14 56.8 (0.49, 0.50) 28.9Example 8 YGD-1(400)12% Comparative compound I: 3.0 60 (0.46, 0.53) 31.5Example 9 YGD-1(400)12% Comparative compound A: 3.63 64.3 (0.47, 0.53)63.2 Example10 PH-1:YGD-1(160:240)16%

Example 50

A compound of HI-1 described below was thermally deposited under vacuumto a thicknesses of 150 Å on the ITO transparent electrode prepared asin Example 1 to form the hole injection layer.

On the hole injection layer, the compound of HT-1 was thermallydeposited under vacuum to a thicknesses of 1150 Å, and then a compoundof HT-3 was deposited under vacuum to a thickness of 500 Å to form ahole transport layer.

Next, on the hole transport layer, the compound 47 prepared in SynthesisExample 15-3 was co-deposited with 5% by weight of a phosphorescentdopant GD-1 to form a light emitting layer having a thickness of 400 Å.

On the light emitting layer, a material of ET-3 was deposited undervacuum to a thickness of 50 Å to form a hole blocking layer, and amaterial of ET-4 and LIQ were deposited under vacuum at a weight ratioof 1:1 to form an electron transport layer. Lithium fluoride (LiF) wassequentially deposited on the electron transport layer in a thickness of10 Å, and Mg was deposited with Ag of 10% by weight on the electrontransport layer to form an electron injection layer having a thicknessof 200 Å. Aluminum was deposited thereon in a thickness of 1000 Å toform a cathode.

In the above process, the vapor deposition rate of the organic materialwas maintained at 0.4 to 0.7 Å/sec, the lithium fluoride of the cathodewas maintained at a deposition rate of 0.3 Å/sec, and the depositionrate of aluminum was maintained at 2 Å/sec. The degree of vacuum duringvapor deposition was maintained at 1×10⁻⁷˜5×10⁻⁸ torr.

Examples 51 to 90

The organic light emitting devices of Examples 51 to 90 were eachfabricated in the same manner as in Example 50, except that thephosphorescent host material and the dopant content at the time offorming the light emitting layer were changed as shown in Tables 4 and 5below.

Comparative Examples 11 to 19

The organic light emitting devices of Comparative Examples 11 to 19 wereeach fabricated in the same manner as in Example 50, except that thephosphorescent host material and the dopant content at the time offorming the light emitting layer were changed as shown in Table 6 below.In this case, the host materials represented by compound A to compound Iused in Comparative Examples are as described above.

Experimental Example 2

After an electric current was applied to each of the organic lightemitting devices fabricated in Examples 50 to 90 and ComparativeExamples 11 to 19, the voltage, efficiency, luminance, color coordinateand life time were measured, and the results are shown in Tables 4 to 6below. In this case, T95 means the time required for the luminance to bereduced to 95% when the initial luminance at a light density of 20mA/cm² was taken as 100%.

TABLE 4 Host: dopant Voltage(V) Efficiency Color Life time (thickness,Å) (@ 10 mA/ (Cd/A) coordinate (T₉₅, h) No. dopant content cm²) (@ 10mA/cm²) (x, y) (@50 mA/cm²) Example compound 47: 4 50.8 (0.349, 0.612)52.9 50 GD-1(400)5% Example compound 48: 4.01 51.1 (0.350, 0.610) 66.451 GD-1(400)5% Example compound 49: 3.98 51.2 (0.350, 0.611) 59.65 52GD-1(400)7% Example compound 50: 4.11 51.8 (0.348, 0.612) 51.8 53GD-1(400)5% Example compound 51: 4.09 50.2 (0.345, 0.612) 51.4 54GD-1(400)5% Example compound 52: 4.1 50.8 (0.348. 0.610) 51.5 55GD-1(400)7% Example compound 16: 4.08 49.1 (0.349, 0.610) 46.7 56GD-1(400)5% Example compound 53: 4.02 51.8 (0.348, 0.612) 55.5 57GD-1(400)7% Example compound 20: 3.97 52.8 (0.349, 0.611) 67.7 58GD-1(400)5% Example compound 54: 4.01 52.4 (0.350, 0.613) 66.2 59GD-1(400)5% Example compound 46: 4.0 52.9 (0.349, 0.612) 65.6 60GD-1(400)5% Example compound 55: 3.99 52.7 (0.350, 0.611) 65.8 61GD-1(400)5% Example compound 56: 3.99 52.4 (0.347, 0.612) 51.3 62GD-1(400)10% Example compound 4: 3.71 55.1 (0.351, 0.609) 110.2 63PH-2:GD-1(200:200)5% Example compound 57: 4.07 52.9 (0.348, 0.612) 79.964 PH-3:GD-1(200:200)5% Example compound 58: 4.2 51.7 (0.347, 0.610)88.7 65 PH-1:GD-1(200:200)5% Example compound 6: 4.21 53.4 (0.347,0.613) 100.1 66 PH-2:GD-1(200:200)5% Example compound 50: 4.17 58.1(0.348, 0.612) 78.9 67 PH-2:GD-1(160:240)7% Example compound 60: 4.2351.7 (0.347, 0.611) 89.2 68 PH-2:GD-1(160:240)5% Example compound 61:4.11 54.2 (0.351, 0.613) 106.2 69 PH-3:GD-1(200:200)5% Example compound62: 4.22 51.9 (0.351, 0.613) 170.7 70 PH-2:GD-1(160:240)5%

TABLE 5 Host: dopant Voltage(V) Efficiency Color Life time (thickness,Å) (@ 10 mA/ (Cd/A) coordinate (T₉₅, h) No. dopant content cm²) (@ 10mA/cm²) (x, y) (@50 mA/cm²) Example compound 63: 4.31 54.2 (0.349,0.613) 134.9 71 PH-3:GD-1(200:200)5% Example compound 64: 4.30 54.3(0.347, 0.612) 135.4 72 PH-1:GD-1(160:240)7% Example compound 65: 4.1952.9 (0.351, 0.613) 170.9 73 PH-2:GD-1(200:200)5% Example compound 66:3.92 52.3 (0.351, 0.613) 171.4 74 PH-1:GD-1(160:240)10% Example compound67: 4.12 54.9 (0.350, 0.611) 128.2 75 PH-2:GD-1(200:200)5% Examplecompound 68: 3.76 56.8 (0.352, 0.609) 104 76 PH-1:GD-1(160:240)5%Example compound 69: 4.10 55.1 (0.351, 0.613) 103.2 77PH-2:GD-1(160:240)7% Example compound 70: 4.17 56.53 (0.351, 0.613)104.5 78 PH-1:GD-1(160:240)5% Example compound 71: 4.24 54.6 (0.346,0.612) 137.9 79 PH-3:GD-1(200:200)7% Example compound 72: 4.32 56.1(0.350, 0.612) 158.8 80 PH-2:GD-1(200:200)5% Example compound 73: 4.4251.24 (0.346, 0.611) 102.5 81 PH-2:GD-1(160:240)5% Example compound 74:4.13 54.7 (0.350, 0.611) 119.9 82 PH-2:GD-1(160:240)10% Example compound75: 4.43 50.35 (0.346, 0.613) 95.2 83 PH-3:GD-1(200:200)7% Examplecompound 76: 4.14 52.8 (0.346, 0.612) 105.7 84 PH-3:GD-1(160:240)10%Example compound 77: 4.35 56.4 (0.347, 0.611) 62.9 85PH-1:GD-1(200:200)5% Example compound 78: 3.92 54 (0.352, 0.609) 81.2 86PH-1:GD-1(200:200)5% Example compound 79: 4.16 56.13 (0.351, 0.613)104.3 87 PH-3:GD-1(160:240)5% Example compound 80: 4.32 50.89 (0.346,0.611) 100.4 88 PH-1:GD-1(160:240)5% Example compound 59: 4.29 53.7(0.347, 0.614) 92.6 89 PH-1:GD-1(160:240)6% Example compound 45: 4.3157.3 (0.350, 0.611) 168.1 90 PH-1:GD-1(160:240)7%

TABLE 6 Host: dopant Voltage(V) Efficiency Color Life time (thickness,Å) (@ 10 mA/ (Cd/A) coordinate (T₉₅, h) No. dopant content cm²) (@ 10mA/cm²) (x, y) (@50 mA/cm²) Comparative compound A: 4.18 51.2 (0.351,0.609) 18.3 Example 11 GD-1(400)5% Comparative compound B: 4.16 46.1(0.352, 0.611) 23.1 Example 12 GD-1(400)5% Comparative compound C: 4.1061.8 (0.351, 0.610) 16.3 Example 13 GD-1(400)5% Comparative compound D:4.21 62.4 (0.351, 0.609) 19.8 Example 14 GD-1(400)5% Comparativecompound E: 5.80 37.1 (0.350, 0.611) 14.7 Example 15 GD-1(400)5%Comparative compound F: 4.08 44.0 (0.352, 0.609) 22.8 Example16GD-1(400)5% Comparative compound G: 4.09 43.2 (0.352, 0.609) 22.0Example 17 GD-1(400)5% Comparative compound H: 4.19 51.0 (0.352, 0.610)27.1 Example 18 GD-1(400)5% Comparative compound I: 4.1 47 (0.349,0.611) 32.2 Example 19 GD-1(400)5%

As shown in Tables 1 to 6 above, the organic light emitting devicesfabricated using the compound according to the present invention as aphosphorescent host material exhibited excellent performance in terms ofdriving voltage, current efficiency, and lifetime as compared with theorganic light emitting devices of Comparative Examples.

Particularly, the organic light emitting devices according to Examplesshowed an increase in lifetime of at least 150% as compared with theorganic light emitting devices according to Comparative Examples 9 and19 using Compound I, which is a phosphorescent host material commonlyused in the art. Further, the organic light emitting devices accordingto Examples 4, 8 and 50 showed an increase in lifetime of about 250% ascompared with the organic light emitting devices according toComparative Examples 1, 6, 11 and 16 using Compounds A and F in whichthe substitution position of triazinyl group is different from that ofthe compound according to the present invention. Further, the organiclight emitting device according to Example 28 also showed an increase inlifetime of about 370% or more as compared with the organic lightemitting device according to Comparative Example 3 using Compound C, andthe organic light emitting device according to Examples 30 and 31 alsoshowed an increase in lifetime of about 250% or more as compared withthe organic light emitting device according to Comparative Example 7using Compound G.

In addition, it could be seen that the driving voltage, currentefficiency and lifetime of the organic light emitting device accordingto Comparative Example 5 using the compound E containing no triazinylgroup were significantly lower than those of the organic light emittingdevice according to Examples. Further, the organic light emitting deviceaccording to Comparative Examples 8 and 18 using the compound Hsubstituted with a dimethylfluorenyl group showed a remarkably low lifetime as compared with the organic light emitting device according toExamples, which is believed to be due to the generation of impuritiesresulting from the formation of radicals by dimethylfluorenyl in thepolymer.

Explanation of Signs 1: substrate 2:anode 3: light emitting layer 4:cathode 5: hole injection layer 6: hole transport layer 7: lightemitting layer 8: electron transport layer

1. A compound of Chemical Formula 1:

wherein in Chemical Formula 1: X₁ is O or S; L₁ is a single bond or anunsubstituted phenylene; L₂ is a single bond, a substituted orunsubstituted phenylene, a substituted or unsubstituted naphthylene, ora substituted or unsubstituted biphenylenyl; Y₁ to Y₃ are eachindependently N or CR₃, provided that at least one of Y₁ to Y₃ is N;Ar_(1a) and Ar_(1b) are each independently a substituted orunsubstituted C₆₋₆₀ aryl or a substituted or unsubstituted C₁₋₆₀heteroaryl containing 1 to 3 heteroatoms selected from the groupconsisting of N, O and S; R₁ and R₂ are each independently hydrogen,deuterium, cyano, or a substituted or unsubstituted C₁₋₁₀ alkyl; each R₃is independently hydrogen, deuterium, halogen, cyano, nitro, amino, asubstituted or unsubstituted C₁₋₆₀ alkyl, a substituted or unsubstitutedC₁₋₆₀ haloalkyl, a substituted or unsubstituted C₁₋₆₀ alkoxy, asubstituted or unsubstituted C₁₋₆₀ haloalkoxy, a substituted orunsubstituted C₃₋₆₀ cycloalkyl, a substituted or unsubstituted C₂₋₆₀alkenyl, a substituted or unsubstituted C₆₋₆₀ aryl, a substituted orunsubstituted C₆₋₆₀ aryloxy, or a substituted or unsubstituted C₁₋₆₀heteroaryl containing at least one heteroatom selected from the groupconsisting of N, O and S; n₁ and n₂ are each independently an integer of0 to 3; and Ar₂ is any one selected from the group consisting of:


2. The compound of claim 1, wherein L₂ is a single bond, or any oneselected from the group consisting of:


3. The compound of claim 1, wherein Y₁ is N, Y₂ is N, and Y₃ is N; or Y₁is N, Y₂ is N, and Y₃ is CH; or Y₁ is N, Y₂ is CH, and Y₃ is N; or Y₁ isN, Y₂ is CH, and Y₃ is CH; or Y₁ is CH, Y₂ is CH, and Y₃ is N.
 4. Thecompound of claim 1, wherein Ar_(1a) and Ar_(1b) are each independentlyany one selected from the group consisting of:

wherein: X₂ is O, S, NZ₄, or CZ₅Z₆; Z₁ to Z₆ are each independentlyhydrogen, deuterium, halogen, cyano, nitro, amino, a substituted orunsubstituted C₁₋₂₀ alkyl, a substituted or unsubstituted C₁₋₂₀haloalkyl, a substituted or unsubstituted C₆₋₂₀ aryl, or a substitutedor unsubstituted C₁₋₂₀ heteroaryl containing one or more heteroatomsselected from the group consisting of N, O and S; c1 is an integer of 0to 5; c2 is an integer of 0 to 4; and c3 is an integer of 0 to
 3. 5. Thecompound of claim 4, wherein Ar_(1a) and Ar_(1b) are each independentlyany one selected from the group consisting of:


6. The compound of claim 1, wherein the compound is any one compoundselected from the group consisting of:


7. An organic light emitting device comprising: a first electrode; asecond electrode provided to face the first electrode; and one or moreorganic material layers provided between the first electrode and thesecond electrode, wherein one or more of the organic material layersinclude the compound of claim
 1. 8. The organic light emitting device ofclaim 7, wherein the organic material layer containing the compound is alight emitting layer.
 9. The organic light emitting device of claim 8,wherein the compound is used as a host material.